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Chemical Structure| 84499-77-4 Chemical Structure| 84499-77-4

Structure of 84499-77-4

Chemical Structure| 84499-77-4

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Product Details of [ 84499-77-4 ]

CAS No. :84499-77-4
Formula : C8H11BrClN
M.W : 236.54
SMILES Code : C[C@H](N)C1=CC=C(Br)C=C1.[H]Cl
MDL No. :MFCD11841191
InChI Key :BQCAANUXMMQVAY-RGMNGODLSA-N
Pubchem ID :53484870

Safety of [ 84499-77-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 84499-77-4 ]

* 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 [ 84499-77-4 ]

[ 84499-77-4 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 50-00-0 ]
  • [ 542-92-7 ]
  • [ 84499-77-4 ]
  • (-)-(1S,1'S)-2-<1'-(4''-Bromophenyl)ethyl>-2-azabicyclo<2.2.1>hept-5-ene [ No CAS ]
  • (-)-(1R,1'S)-2-<1'-(4''-Bromophenyl)ethyl>-2-azabicyclo<2.2.1>hept-5-ene [ No CAS ]
  • 2
  • [ 911372-67-3 ]
  • [ 84499-77-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In 1,4-dioxane; methanol; at 20.0℃; for 2.0h; A stirred solution of (R)-N-((S)-l-(4-bromophenyl)ethyl)-2-methylpropane-2- sulfinamide from step 2 (7.03 g, 23.1 mmol) in MeOH (33 mL) at 20 0C was treated with HCl (11.5 mL, 4 M in dioxane, 46 mmol). NOTE: exothermic. The mixture was stirred at 20 0C for 2 h, then concentrated in vacuo. The colourless solid was dried under vacuum at 40 C for 1 h, to yield the amine as its hydrochloride salt, containing some ^-butyl methyl sulfoxide.
  • 3
  • [ 911372-48-0 ]
  • [ 84499-77-4 ]
  • 5
  • [ 84499-77-4 ]
  • [ 111-44-4 ]
  • [ 494773-21-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 38.0h; A suspension of (S)-I -(A-bromophenyl)ethanamine hydrochloride from step 3 (2.00 g,8.46 mmol), 2-chloroethyl ether (2.0 mL, 17.1 mmol) and K2CO3 (3.53 g, 25.5 mmol) in DMF (30 mL) was stirred at 100 0C for 38 h. After cooling to 20 0C, the mixture was partitioned between water (30 mL) and ether (30 mL). The aqueous layer was extracted with ether (3 x 30 mL); the combined organic extracts were washed with water (30 mL), dried (Na2SO4) and concentrated in vacuo. Purification by chromatography (20% EtOAc-hexanes) yielded the morpholine (270 mg, 1.00 mmol, 13% over 2 steps) as a yellow liquid.
  • 6
  • [ 84499-77-4 ]
  • [ 73183-34-3 ]
  • [ 494773-21-6 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 90.0℃; for 17.0h;Inert atmosphere; Sealed tube; A mixture of (S)-4-(l-(4-bromophenyl)ethyl)morpholine from step 4 (270 mg, 1.00 mmol), bis(pinacolato)diboron (330 mg, 1.30 mmol), PdCl2(dppf) (41 mg, 50 μmol) and KOAc (128 mg, 1.30 mmol) and dioxane (2.6 mL) in a reaction tube was purged with nitrogen gas for 10 min. The tube was sealed under nitrogen and the mixture stirred at 90 0C for 17 h. The brown mixture was filtered through Celite, washing with 30 mL EtOAc. The filtrate was concentrated and the residue was used immediately without further purification.
  • 7
  • [ 24424-99-5 ]
  • [ 84499-77-4 ]
  • [ 847728-89-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20.0℃; Description 1 : (S)-tert-butyl (1-(4- romophenyl)ethyl)carbamate (D1)A mixture of (S)-(-)-1 -(4-Bromophenyl)ethylamine hydrochloride (9 g, 38.0 mmol, available from Bepharm Ltd No.B157615), di-tert-butyl dicarbonate (8.72 g, 1 .05 mmol), and triethylamine (16ml, 1 14 mmol) in dichloromethane (120ml) was stirred at room temperature overnight. The mixture was diluted with dichloromethane (200ml) and washed with water (100ml). The organic solution was dried over Na2S04 and solvents were evaporated in vacuo to afford the title compound (D1) (12.7 g) as a white solid.1 H NMR (400MHz ,CHLOROFORM-d) δ (ppm): 7.47- 7.42 (2H, m), 7.18 (2H, d, J= 8.4 Hz), 5.30 (2H, br s), 1 .41 (12H, br s).
12.7 g With triethylamine; In dichloromethane; at 20.0℃; A mixture of (S)-(-)-1-(4-Bromophenyl)ethylamine hydrochloride (9 g, 38.0 mmol, available from Bepharm Ltd B157615), di-tert-butyl dicarbonate (8.72 g, 1.05 mmol), and triethylamine (16 ml, 114 mmol) in dichloromethane (120 ml) was stirred at room temperature overnight. The mixture was diluted with dichloromethane (200 ml) and washed with water (100 ml). The organic solution was dried over Na2SO4 and solvents were evaporated in vacuo to afford the title compound (D1) (12.7 g) as a white solid.
  • 8
  • [ 84499-77-4 ]
  • [ 847728-90-9 ]
  • 9
  • [ 84499-77-4 ]
  • methyl (S)-4-(1-aminoethyl)benzoate hydrochloride [ No CAS ]
  • 10
  • [ 84499-77-4 ]
  • [ 1380754-50-6 ]
  • 11
  • [ 1039750-63-4 ]
  • [ 84499-77-4 ]
  • 12
  • [ 1438984-03-2 ]
  • [ 84499-77-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water; In methanol; at 20.0℃; for 4.0h; (S)-N-((S)- 1 -(4-bromopheny3)ethyi)-2-methylpropane-2-sulfinamide (170 mg, 0.56 mmol) was dissolved in methanol (2 mL) followed by addition of con.HCl ( 1 mL). The mixture was stirred at T for 4 h and then was concentrated and evaporated with toluene twice to afford the titled compound. 1 i N .'vi R (METHANOL-d4) δ 7.57 - 7.70 (m, 2H), 7.36 - 7.45 (m, 2H), 4.48 (q, J = 6.7 Hz, Hi), 1.62 - 1.68 (m, 4H) LC-MS: m/z 200.1 (M+H) +
With hydrogenchloride; water; In methanesulfonic acid; at 20.0℃; for 4.0h; (S)-N-((S)- 1 -(4-bromophenyl)ethyl)-2-methylpropane-2-sulfinaniide (170 mg, 0.56 mmol) was dissolved in methanol (2 mL) followed by addition of con.HCl (1 mL). The mixture was stirred at RT for 4 h and then was concentrated and e vaporated with toluene twice to afford the titled compound. Ή NMR (METHANOL-d4) δ 7.57 - 7.70 (m, 2H), 7.36 - 7.45 (m, 2H), 4.48 (q, J - 6.7 Hz, I Fi), 1 .62 - 1.68 (m, 4H) LC-MS: m/z 200. i i M H i
  • 13
  • [ 24424-99-5 ]
  • [ 84499-77-4 ]
  • [ 847728-90-9 ]
 

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Technical Information

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