19935-81-0|1-(1-Bromoethyl)-4-nitrobenzene| Ambeed

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Quality Control of [ 19935-81-0 ] Purity: 97% SDS Specification

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Product Details of [ 19935-81-0 ]

CAS No. :	19935-81-0
Formula :	C₈H₈BrNO₂
M.W :	230.06
SMILES Code :	O=[N+](C1=CC=C(C(Br)C)C=C1)[O-]
MDL No. :	MFCD11634400
InChI Key :	LLTKPPRBFXTUKH-UHFFFAOYSA-N
Pubchem ID :	11020679

Safety of [ 19935-81-0 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Computational Chemistry of [ 19935-81-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	52.91
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.9
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.97
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.73
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.81
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.82
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.25

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.38
Solubility	0.0969 mg/ml ; 0.000421 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.6
Solubility	0.0584 mg/ml ; 0.000254 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.07
Solubility	0.194 mg/ml ; 0.000845 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.59 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	3.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.33

Application In Synthesis of [ 19935-81-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 19935-81-0 ]

[ 19935-81-0 ] Synthesis Path-Downstream 1~35

1
[ 79-46-9 ]
[ 19935-81-0 ]
[ 141-52-6 ]
[ 100-19-6 ]

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 3482,3485.

2
[ 100-12-9 ]
[ 19935-81-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With Oxone; water; potassium bromide; In dichloromethane; at 20℃; for 6.0h;Irradiation; Sealed tube;	General procedure: KBr (29.8 mg, 0.25 mmol, 1.0 equiv), 1-ethyl-4-nitrobenzene (1a) (41.6 mg, 0.275 mmol, 1.1 equiv), Oxone (153.9 mg, 0.25 mmol, 1.0 equiv), CH2Cl2 (0.25 mL) and H2O (180.0 mg, 0.18 mL, 40.0 equiv) were added, in accordance with the order, to a 15-mL oven-driedtube. The reaction tube was equipped with a magnetic stir bar and sealed with a Teflon-lined cap at once after the addition of the H2O. Then, the tube was placed on a magnetic stirrer (speed 300 rpm) and irradiated with a 0.5 W LED at a distance of 5 cm for 20 h at rt. After the reaction was finished, the reaction mixture was quenched with Na2SO3. Water (15 mL) was added and the mixture extracted with CH2Cl2 (3 × 5 mL). The organic phase was combined and dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give the crude product that was purified by flash column chromatography (petroleum ether/EtOAc mixtures). Compound 3a was obtained as a light yellow solid; yield: 53.6 mg (93%).
94%Chromat.	With Oxone; potassium bromide; In water; acetonitrile; at 45℃;	General procedure: To a solution of aromatic compound 1a-q (1 mmol) in CH3CN (6 mL) and H2O (0.5 mL) were added KBr (0.5 mmol) and Oxone (2.2 mmol), and the mixture was stirred at 45C. After completion (monitored by TLC), the reaction mixture was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous Na2S2O3 and brine, dried over anhydrous Na2SO4. Removal of the solvent under vacuum afforded the crude product, which was purified by column chromatography using hexane/ethyl acetate as eluent (20 - 80 : 1).

References: [1]Synthesis,2018,vol. 50,p. 4933 - 4939.
[2]Journal of Organic Chemistry,1998,vol. 63,p. 6023 - 6026.
[3]Organic Letters,2012,vol. 14,p. 2414 - 2417.
[4]Journal of the American Chemical Society,1949,vol. 71,p. 3482,3485.
[5]Journal of general chemistry of the USSR,1962,vol. 32,p. 2982 - 2984.
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3033 - 3035.
[6]Tetrahedron Letters,2012,vol. 53,p. 4418 - 4421.
[7]Chemical Communications,2019,vol. 55,p. 4238 - 4241.

3
[ 19935-81-0 ]
[ 109-89-7 ]
[ 100316-97-0 ]

References: [1]Journal of Organic Chemistry,1956,vol. 21,p. 1024.

4
[ 19935-81-0 ]
[ 29342-38-9 ]

References: [1]Journal of the American Chemical Society,1970,vol. 92,p. 4689 - 4699.

5
[ 1083-48-3 ]
[ 19935-81-0 ]
[ 83118-61-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 2077 - 2086.

6
[ 6531-13-1 ]
[ 19935-81-0 ]

Yield	Reaction Conditions	Operation in experiment
49%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 1.5h;Heating / reflux;	Asolution of 1-ethyl-4-nitrobenzene (10.0 g, 66 mmol), N-bromosuccinamide (11.8g, 66 mmol) and benzoyl peroxide (160 mg, 0.66 mmol) in CCI4 (100 (mL) was heated to reflux for 1.5 hrs. The reaction mixture was then cooled to 0 0C and filtered through a fritted funnel. The isolated solid was washed once with hexane (50 mL) and the combined filtrates were concentrated and purified by column chromatography (2-5% EtOAc/Hex) to afford 1-(1-bromoethyl)-4-nitrobenzene (7.52 g, 49%). 1H NMR (400 MHz, ' CDCI3) delta 8.21 (d, 2 H), 7.58 (d, 2 H), 5.22 (q, 1 H), 2.05 (d, 3 H).

References: [1]Patent: WO2008/23235,2008,A1 .Location in patent: Page/Page column 57.
[2]Journal of the American Chemical Society,1968,vol. 90,p. 418 - 426.
[3]Journal of Organic Chemistry,1969,vol. 34,p. 1086 - 1089.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 68 - 70.
[5]Journal of the American Chemical Society,1983,vol. 105,p. 320 - 324.
[6]Angewandte Chemie - International Edition,2019,vol. 58,p. 10330 - 10334.
Angew. Chem.,2019,vol. 131,p. 10437 - 10442,6.

7
[ 19935-81-0 ]
[ 100-13-0 ]
[ 19935-81-0 ]

References: [1]Canadian Journal of Chemistry,1987,vol. 65,p. 363 - 371.

8
[ 19935-81-0 ]
[ 123-54-6 ]
[ 116159-79-6 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 1469 - 1470.

9
[ 19935-81-0 ]
[ 105-53-3 ]
[ 37556-09-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 68 - 70.

10
[ 19935-81-0 ]
[ 90050-69-4 ]

References: [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 2982 - 2984.
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3033 - 3035.

11
[ 19935-81-0 ]
[ 75-07-0 ]
[ 18755-62-9 ]

References: [1]Journal of Organic Chemistry,1969,vol. 34,p. 1086 - 1089.

12
[ 110-86-1 ]
[ 19935-81-0 ]
1-[1-(4-Nitro-phenyl)-ethyl]-pyridinium; bromide [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 3243 - 3246.

15
[ 19935-81-0 ]
[ 100-13-0 ]
[ 64747-67-7 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 2761 - 2763.

16
[ 110-01-0 ]
[ 19935-81-0 ]
C₁₂H₁₆NO₂S⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 5871 - 5873.

17
[ 19935-81-0 ]
[ 124-40-3 ]
[ 42142-22-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 25℃; for 17.0h;	To a solution of 1-(1-bromoethyl)-4-nitrobenzene (1.3 g, 5.65 mmol) in DMF (10 mL) was added dimethyl amine (14.1 mL of 2.0 M solution in THF, 28.3 mmol) and potassium carbonate (2.34 g, 17 mmol). Reaction was stirred at 25 0C for 17 hrs. Subsequently, EtOAc {50 mL) and water (50 mL) were added. The organic layer was separated, washed with brine and concentrated to afford N,N-dimethy.-1-(4- nitrophenyl)ethanamine (0.98 g, 89%). 1H NMR {400 MHz, CDCI3) delta 8.18 (d, 2-H), 7.51 (d, 2 H), 3.38 (q, 1 H), 2.10 (S, 6 H), 1.36 (d, 3 H).

References: [1]Patent: WO2008/23235,2008,A1 .Location in patent: Page/Page column 57.

18
[ 19935-81-0 ]
[ 111654-20-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 68 - 70.

19
[ 19935-81-0 ]
[ 111654-24-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 68 - 70.

20
[ 19935-81-0 ]
[ 105838-72-0 ]

References: [1]Journal of Organic Chemistry,1956,vol. 21,p. 1024.

21
[ 110-91-8 ]
[ 19935-81-0 ]
[ 96921-35-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 16.0h;	A mixture of 1-(1-bromo-ethyl)-4-nitro-benzene (1.24 g, 5.43 mmol), potassium carbonate (2.25 g, 16.3 mmol) and morpholine (1.2 mL, 13.6 mmol) in DMF (10 mL) was stirred at room temperature for 16h, then evaporated. The residue was suspended in ethyl acetate, washed with water and brine, dried (sodium sulfate) and evaporated to provide 4-[1-(4-nitro-phenyl)-ethyl]-morpholine (1.225 g, 95% yield) as a yellow oil. 1H-NMR (DMSO-d6, 500 MHz) 8.19 (d, 2H), 7.16 (d, 2H), 3.56 (m, 5H), 2.41 (m, 2H), 2.26 (m, 2H), 1.29 (d, 3H) ppm; MS (FIA) 237.2 (M+H); HPLC (Method A) 2.248 min.

References: [1]Patent: WO2004/46120,2004,A2 .Location in patent: Page 174.

22
[ 128-08-5 ]
[ 100-12-9 ]
[ 19935-81-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With dibenzoyl peroxide; In tetrachloromethane; for 1.0h;Heating / reflux;	A mixture of 1-ethyl-4-nitro-benzene (3.4 mL, 25 mmol), N-bromosuccinimide (4.38 g, 24.6 mmol) and benzoylperoxide (0.04g, 0.18 mmol) in carbon tetrachloride (30 mL) was refluxed 1h, cooled and filtered, washing with 1:1 ethyl acetate : hexanes. The filtrate was evaporated and purified by flash chromatography (SiO2) eluted with 2:98 ethyl acetate : hexanes to provide 1-(1-bromo-ethyl)-4-nitro-benzene (5.18 g, 90% yield) as a yellow oil. 1H-NMR (CDCl3, 500 MHz) 8.22 (d, 2H), 7.62 (d, 2H), 5.22 (q, 1H), 2.08 (d, 3H) ppm; HPLC (Method A) 3.837 min.

References: [1]Patent: WO2004/46120,2004,A2 .Location in patent: Page 173;174.

23
Na₂ S₂ O_3.5 H₂ O [ No CAS ]
Na₂ S_9.H₂ O [ No CAS ]
sodium 4-nitrophenylethyl-thiosulfate [ No CAS ]
[ 19935-81-0 ]
bis[2-(4-aminophenyl)ethyl]disulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water; ethyl acetate;	To a refluxing solution of 4-nitrophenylethylbromide (23 g) in a mixture of 280 mL of methanol and 70 mL of water was added a solution of Na2 S2 O3.5 H2 O (31 g) in 75 mL of water. A further 60 mL of water was then added to the reaction mixture. Refluxing conditions were continued for 5 hours. The resulting pale yellow solution was allowed to cool to room temperature. Methanol was removed from the solution on a rotary evaporator leaving a white crystalline aqueous slurry. Addition of 300 mL of water to the slurry yielded a slightly cloudy solution. To this aqueous solution of sodium 4-nitrophenylethyl-thiosulfate was added a solution of Na2 S9.H2 O (120 g) in 300 mL of water. The reaction mixture rapidly grew cloudy and slightly yellow and, after several minutes of stirring, a white precipitate formed. This slurry was heated to reflux for 18 hours then cooled An orange oil was present which was extracted with several portions of ethyl acetate. The ethyl acetate ex were combined, dried over MgSO4, and filtered. Removal of the ethyl acetate yielded 12 g of bis(2-(4-aminophenyl)ethyl) disulfide as an orange oil.

References: [1]Patent: US5900029,1999,A .

24
1,3-dimethyl-6-(4-[2-hydroxy-4-phenylbutyl)piperazin-1-yl)-2,4(1H,3H)-pyrimidinedione.hydrochlordide [ No CAS ]
[ 19935-81-0 ]
[ 108-59-8 ]
dimethyl 1-(4-nitrophenyl)ethylmalonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide;	(2) Preparation of dimethyl 1-(4-nitrophenyl)ethylmalonate 1.18 g of sodium hydride (60% and oily) was suspended in 20 ml of dimethyl sulfoxide, and 3.9 g of dimethyl malonate was added dropwise thereto under ice cooling. After the addition, the temperature of the reaction solution was elevated to room temperature, and 3.4 g of 1-(4-nitrophenyl)ethyl bromide synthesised in the above-mentioned section (1) was added thereto, followed by stirring at room temperature for 20 hours in an atmosphere which was shielded from light. The resulting reaction mixture was poured into 1N hydrochloric acid slowly, and the solution was then extracted twice with 50 ml of ether. Extracts were joined together, washed with water and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The solution was then evaporated to dryness, thereby obtaining 3.9 g of dimethyl 1-(4-nitrophenyl)ethylmalonate in an oily state. Analytical results of the obtained malonic derivative NMR (CDCl3) delta ppm: 1.38 (m, 3 H), 3.53 (s, 3 H), 3.81 (s, 3 H), 3.63-3.76 (m, 2 H), 7.43 (d, 2 H), 8.21 (d, 2 H).

References: [1]Patent: US5308848,1994,A .

25
aqueous potassium carbonate [ No CAS ]
[ 100-19-6 ]
[ 19935-81-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; phosphorus tribromide; sodium borohydrid; In ethanol; dichloromethane;	(1) Preparation of 1-(4-nitrophenyl)ethyl bromide 6.0 g of p-nitroacetophenone was dissolved in 100 ml of ethanol, and 0.75 g of sodium borohydride was added thereto under ice cooling. Afterward, the reaction solution was stirred at room temperature for 2 hours, and 1 ml of 0.1N hydrochloric acid was added thereto so as to bring the reaction to an end. This reaction mixture was concentrated under reduced pressure, and 100 ml of 0.5N hydrochloric acid was added to the resulting residue and extraction was then carried out twice with 50 ml of ether. The resulting ether layers were joined together, washed with water, and then dried over anhydrous sodium sulfate, and the solvent was distilled off. Afterward, the resulting residue was dissolved in 100 ml of methylene chloride. 7.2 g of phosphorus tribromide was added dropwise to the solution under ice cooling, followed by stirring at room temperature for 10 hours. Next, an aqueous potassium carbonate solution was added to the reaction solution to neutralize the same, and the resulting methylene chloride layer was separated, washed with water, and then dried over anhydrous sodium sulfate. Afterward, the solvent was distilled off under reduced pressure, and the resulting residue was purified through a silica gel column chromatograph (chloroform/hexane=2/1 in volume ratio), thereby obtaining 3.5 g of oily 1-(4-nitrophenyl)ethyl bromide. Analytical results of the obtained bromide derivative NMR (CDCl3) delta ppm: 2.06 (d, 3 H), 5.23 (q. 1 H), 7.60 (d, 2 H), 8.20 (d, 2 H).

References: [1]Patent: US5308848,1994,A .

26
[ 100-27-6 ]
[ 603-35-0 ]
[ 19935-81-0 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; carbon tetrabromide;	EXAMPLE 4 Preparation of 2,2 di (4-nitrophenyl) ethyl bromide To a stirred solution of 2,2 di (4-nitrophenyl) ethanol (0.155 g, 0.54 mmoles) produced by the process of Example 2 in carbon tetrabromide (1.08 moles, 0.362 g) was added triphenyl phosphine (21.08 mmoles, 0.289 g). The originally clear liquid turned yellow immediately, whilst thin layer chromatography indicated that no starting material was present. The solvent was removed under vacuum to give, after flash chromatography (eluent, 1:4 ethyl acetate: petrol ether), the bromide in crystalline form (yield 75%); recrystallisation was from methylene chloride.

References: [1]Patent: US5164515,1992,A .

27
[ 19935-81-0 ]
[ 33953-37-6 ]
[ 36806-79-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In isopropyl alcohol; Petroleum ether; benzene;	EXAMPLE 22 1-[2-(p-Nitrophenyl)ethyl]-4-benzamidopiperidine p-Nitrophenylethyl bromide (1.15 g.) was refluxed for 20 hours in isopropylalcohol (75 ml.) with 4-benzamidopiperidine (1.032 g.) and anhydrous potassium carbonate (1.037 g.). The mixture was filtered hot, refrigeratedand product was filtered off (547 mg.), washed with cold isopropyl alcohol and ether. The filtrate was evaporated to yield more product (1.4 g.). Recrystallisation from a mixture of benzene and petroleum ether (b.p. 40-60 C) gave the title compound, m.p. 209-216 C. (Found: C, 68.2; H, 6.7; N, 11.8. C20 H23 N3 O3 requires C, 68.0; H, 6.6; N, 11.9%). The product exhibits hypotensive activity and also depressant and anti-tremorine activities.
	With potassium carbonate; In Petroleum ether; benzene;	EXAMPLE 22 1-[2-(p-Nitrophenyl)ethyl]-4-benzamidopiperidine p-Nitrophenylethyl bromide (1.15 g.) was refluxed for 20 hours in isopropyl alcohol (75 ml.) with 4-benzamidopiperidine (1.032 g.) and anhydrous potassium carbonate (1.037 g.). The mixture was filtered hot, refrigerated and product was filtered off (547 mg.), washed with cold isopropyl alcohol and ether. The filtrate was evaporated to yield more product (1.4 g.). Recrystallisation from a mixture of benzene and petroleum ether (b.p. 40-60 C.) gave the title compound, m.p. 209-216 C. (Found: C, 68.2; H, 6.7; N, 11.8. C20 H23 N3 O3 requires C, 68.0; H, 6.6; N, 11.9%). The product exhibits hypotensive activity and also depressant and anti-tremorine activities.

References: [1]Patent: US3992389,1976,A .
[2]Patent: US4029801,1977,A .

28
[ 19935-81-0 ]
[ 1007-27-8 ]
[ 1066-44-0 ]
[ 169059-35-2 ]