Structure of 80567-00-6
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 80567-00-6 |
Formula : | C6H14ClNO |
M.W : | 151.63 |
SMILES Code : | CC1OC(C)CNC1.[H]Cl |
MDL No. : | MFCD28099212 |
InChI Key : | SFEUYYPUMLXCLF-UHFFFAOYSA-N |
Pubchem ID : | 19374754 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; | EXAMPLE 1 Synthesis of 4-[3-(3-benzoylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (Compound No.1). 0.7 g of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong>, a mixture of cis-trans isomers, are dissolved in 8 cc of methanol. 0.069 g of potassium hydroxide and 1 g of 3-(3-benzoylphenyl)-2-methylpropanal are added. After 15 minutes a solution of 0.084 g of sodium cyanoboron hydride in 1 cc of methanol are added dropwise and after a further 30 minutes 0.27 g of potassium hydrate in powder form are added. The mixture is filtered on celite and the solvent evaporated at reduced pressure. The raw product is purified by silica gel chromatography, with hexane/ethyl acetate=9/1 as eluant, to obtain 0.8 g of compound 1, cis isomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With paraformaldehyde;hydrogenchloride; In ethanol; | EXAMPLE 1 This Example illustrates the preparation of 6-methoxy-2-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalene (compound No. 11 of Table 1). 6-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one (17.6 g, 0.1 mol), <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> (15.1 g, 0.1 mol), and paraformaldehyde (6.0 g, 0.2 mol) were refluxed together in ethanol (50 ml) with concentrated hydrochloric acid (0.25 ml) as a catalyst for 3 hours. The reaction was cooled and poured into water containing concentrated hydrochloric acid (5 ml) and extracted with ether (200 ml). The aqueous solution was cooled in ice and neutralised with sodium hydroxide solution (10%) then extracted with ether (2*200 ml) dried over magnesium sulphate and evaporated under reduced pressure to give a residue which was recrystallized from petrol (60-80) to give 6-methoxy-2-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one a white crystalline solid (10 g, 33% yield) melting at 110 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With paraformaldehyde;hydrogenchloride; In ethanol; water; | EXAMPLE 3 This Example illustrates the preparation of 7-tert-butyl-3-cis-(2,6-dimethylmorpholinomethyl)-1,2-dihydronaphthalene (Compound No. 2 in Table I). 2,6-Dimethylmorpholine hydrochloride (12.1 g, 0.08 mol), 6-tert-butyl-1,2,3,4-tetrahydronaphthalen-1-one (8.1 g, 0.04 mol) and paraformaldehyde (2.4 g, 0.08 mol) were refluxed together in ethanol (150 ml) with concentrated hydrochloric acid (1 ml) as a catalyst for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water then extracted with diethyl ether. The resulting aqueous solution was neutralised with sodium bicarbonate and extracted with diethyl ether (2*200 ml); the ethereal extracts were dried over anhydrous magnesium sulphate and concentrated under reduced pressure to give an orange oil. This oil was purified by hplc (silica eluted with ethyl acetate/petroleum ether 1:1) to give 6-tert-butyl-2-cis-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one (5.1 g, 39%). |
39% | With paraformaldehyde;hydrogenchloride; In ethanol; water; | EXAMPLE 2 This Example illustrates the preparation of 6-tert-butyl-2-cis-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalene (Compound No. 21 in Table I). 2,6-Dimethylmorpholine hydrochloride (12.1 g, 0.08 mol), 6-tert-butyl-1,2,3,4-tetrahydronaphthalen-1-one (8.1 g, 0.04 mol), and paraformaldehyde (2.4 g, 0.08 mol) were refluxed together in ethanol (150 ml) with concentrated hydrochloric acid (1 ml) as a catalyst for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water then extracted with diethyl ether. The resulting aqueous solution was neutralised with sodium bicarbonate and extracted with diethyl ether (2*200 ml); the ethereal extracts were dried over anhydrous magnesium sulphate and concentrated under reduced pressure to give an orange oil. This oil was purified by hplc (silica eluted with ethyl acetate/petroleum ether 1:1) to give 6-tert-butyl-2-cis-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one (5.1 g, 39%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; | EXAMPLE 2 Synthesis of 4-[3-(3-benzoylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (Compound No. 1). 0.7 g of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong>, a mixture of cis-trans isomers, are dissolved in 8 ml of methanol, whereafter 0.069 g of potassium hydroxide and 1 g of 3-(3-benzoylphenyl)-2-methylpropanal are added. After 15 minutes a solution of 0.084 g of sodium cyano borohydride in 1 ml of methanol is added dropwise and after a further 30 minutes 0.27 g of potassium hydroxide in powder form are added. The mixture is filtered on celite and the solvent evaporated at reduced pressure. The crude product is purified by silica gel chromatography, with hexane/ethyl acetate = 9/1 as eluent, to obtain 0.8 g of compound 1, cis isomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; for 24h;Heating / reflux;Product distribution / selectivity; | Step 3: 5-Bromo-2-(2,6-dimethyl-morpholin-4-yl)-3,4-difluoro-benzaldehyde. To a solution of 5-bromo-2,3,4-trifluoro-benzaldehyde (11.5g, 48mmol) in dry acetonitrile (18OmL) was added Et3N (16.7mL, 120mmol) and 2,6-dimethylmorpholine, HCI Salt(8.3g, 53mmol). The reaction mixture was refluxed for 24 h. The solution was allowed to cool to room temperature and then poured into a saturated solution of NaHCO,,. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO . and concentrated to give an orange oil (15 g). Slurry of the crude in heptane yielded 11.92g of a yellow solid. 1 H-NMR (500 MHz, CDCI3) d 10.36 (s, 1H), 7.82 (dd, 1 H), 4.19 (m, 2H), 3.3 (d, 2H), 2.97 (dd,2H),1.30 (d, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2: 2,6-DimethyI-morpholine, HCI Salt. 4-Benzyl-2R,6R-(trans)-dimethyl- morpholine (15g, 73 mmol) was charged to an autoclave and MeOH (800 mL) added. Pd/C (3.5 g) was added and the mixture was stirred at room temperature overnight under 3.5 bars of pressure of H2. The mixture was then filtered through celite followed by the addition of HCI 2M in Et2O (47 mL,1.3 eq, 95 mmol). This filtrate was then concentrated to give the 8.3 g of the moφholine salt. 1 H-NMR (500 MHz, CDCI3) d 4.26 (m, 2H), 3.25(m, 2H), 2.94 (m, 2H), 1.39 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33.16% | 0.165g (1.1mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.3g (10mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 1hr. After the solid was dissolved, 0.214g (1.0mmol) of 4-(4-trifluoromethylphenyl)-3-buten-2-one (prepared as described in preparation 16) was added to the above reaction mixture. The solution was further refluxed and stirred for 12hr. After cooling with ice-water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol and dried to give 0.125g of white crystals, yield: 33.16 %, mp: 203-205C . 1HNMRδppm (DMSO-d6): 1.09(d, 6H, J=6.6Hz, 2CH3-CH), 2.47-2.68(m, 6H, 3NCH2), 3.33-3.43(m, 2H, COCH2), 3.85(q, 2H, J=6.6Hz, 2CH3-CH), 7.04(d, 1H, J=16.2Hz, =CHCO), 7.759(d, 1H, J=16.2Hz, CH=), 7.819(d, 2H, J=8.4Hz, ArHAA'), 7.955(d, 2H, J=8.4Hz, ArHBB')o FAB-MS (m/z): 342.2(M++1 ), 274.2(M+-F3C+1), 128.4(M+-213). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25.3% | 0.5g (3.3mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.9g (30mmol) of paraformaldehyde were dissolved in anhydrous ethanol (15ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 1hr. After the solid was dissolved, 0.619g (3.0mmol) of 4-(3-ethoxy-4-hydroxyphenyl)-3-buten-2-one (prepared as described in preparation 5) was added to the above reaction mixture. The solution was further refluxed and stirred for 9hr. After cooling with cold water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol - methanol and dried to give 0.281g of white crystals, yield 25.3 %, mp: 198-201C. 1HNMRδppm (DMSO-d6): 1.10(d, 6H, J=6.6Hz, 2xCHCH3), 1.29-1.33 (t, 3H, J=7.2Hz, OCH2CH3), 2.47-2.61(m, 6H, 2NCH2), 2.62-2.69 (t, 2H, COCH2), 3.25-3.46(q, 2H, J=7.2Hz, OCH2CH3), 3.87(q, 1H, OH, D2O exchange), 3.95(q, 2H, J=6.6Hz, 2xCHCH3), 6.73(d, 1H, J=16.2Hz, =CHCO), 6.84(d, 1H, J=8.1Hz, ArH), 7.15(q, 1H, J=8.1Hz, J=1.5Hz, ArH), 7.29(s, 1H, ArH), 7.59(d, 1H, J=16.2Hz, CH=). FAB-MS (m/z): 334.3(M++1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.5% | 0.303g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.6g (20mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 1hr. After the solid was dissolved, 0.44g (2.0mmol) of 4-(3-methoxy-4-ethoxyphenyl)-3-buten-2-one (prepared as described in preparation 6) was added to the above reaction mixture. The solution was further refluxed and stirred for 11hr. TLC showed the reaction was completed. After cooling with cold water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol - methanol and dried to give 0.15g of white crystals, yield: 19.5 %, mp: 191-194C. 1HNMRδppm (DMSO-d6): 1.06-1.12(d, 6H, J=6.6Hz, 2xCHCH3), 1.29-1.34(t, 3H, J=7.2Hz, OCH2CH3), 2.02-3.20(m, 6H, 3NCH2), 3.24-3.46(q, 2H, J=7.2Hz, OCH2CH3), 3.79(s, 3H, OCH3), 4.05(q, 2H, J=6.6Hz, 2xCHCH3), 6.61(d, 1H, J=16.2Hz, =CHCO), 6.98(d, 1H, J=8.4Hz, ArH), 7.25(d, 1H, J=8.4Hz, ArH), 7.32(d, 1H, J=8.4Hz, ArH), 7.64(d, 1H, J=16.2Hz, CH=). MS (m/z): 347(M+, 42), 232(M+-115, 94), 190((M+-115-14, 10). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36.6% | 0.303g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.4g (13mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 2.0hr. After the solid was dissolved, 0.384g (2.0mmol) of 4-(3-hydroxy-4-methoxyphenyl)-3-buten-2-one (preparedas described in preparation 20) was added to the above reaction mixture. The solution was further refluxed and stirred for 15hr. TLC showed the reaction was completed. After cooling with cold water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol and dried to give 0.26g of white crystals, yield: 36.6 %, mp: 194-196C. 1HNMRδppm (DMSO-d6): 1.09(d, 6H, J =6.6Hz, 2xCHCH3), 2.47-2.68 (m, 6H, 3NCH2), 3.24-3.46(t, 2H, COCH2), 3.95(q, 2H, J=6.6Hz, 2xCHCH3), 6.61(d, 1H, J=16.2Hz, =CHCO), 6.98(d, 1H, J=8.4Hz, ArH), 7.14(d, 2H, J=8.4Hz, ArH), 7.57(d, 1H, J=16.2Hz, CH=). MS (m/z): 319(M+, 40), 204(M+-115, 35), 190(M+-115-14, 10). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.8% | 0.303g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.4g (13mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 2hr. After the solid was dissolved, 0.36g (2.0mmol) of 4-(4-chlorophenyl)-3-buten-2-one (prepared as described in preparation 1) was added to the above reaction mixture. The solution was further refluxed and stirred for 13hr. TLC showed the reaction was completed. After cooling with ice-water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol and dried to give 0.37g of white crystals, yield: 53.8 % , mp: 218-220C. 1HNMRδppm (DMSO-d6): 1.09(d, 6H, J=6.6Hz, 2 x CHCH3), 2.47-2.68 (m, 6H, 3NCH2), 3.24-3.46(t, 2H, COCH2), 3.95(q, 2H, J=6.6Hz, 2 x CHCH3), 6.92(d, 1H, J=16.2Hz, =CHCO), 7.49(d, 2H, J=8.4Hz, ArHAA'), 7.69(d, 1H, J=16.2Hz, CH=), 7.79(d, 2H, J=8.4Hz, ArHBB'). MS (m/z): 307(M+, 20), 192(M+-114-H, 24), 165(M+-142, 60). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.2% | 0.30g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.15g (5mmol) of paraformaldehyde were dissolved in anhydrous ethanol (10ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 2hr. After the solid was dissolved, 0.38g (2.0mmol) of 4-(3,4-methylenedioxyphenyl)-3-buten-2-one (prepared as described in preparation 15) was added to the above reaction mixture. The solution was further refluxed and stirred for 11hr. After cooling with cold water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol - methanol and dried to give 0.46g of white crystals, yield: 65.2 %, mp: 178-181C. 1HNMRδppm (DMSO-d6): 1.11(d, 6H, J=6.6Hz, 2 x CHCH3), 2.47-2.68 (m, 6H, 3NCH2), 3.26-3.46(t, 2H, COCH2), 3.89(q, 2H, J=6.6Hz, 2 x CHCH3), 6.08(s, 2H, OCH2O), 6.77(d, 1H, J=16.2Hz, =CHCO), 6.98(d, 1H, J=8.4Hz,ArH), 7.20(dd, 1H, J=8.4Hz, J=1.5Hz, ArH), 7.39(d, 1H, J=1.5Hz, ArH), 7.61(d, 1H, J=16.2Hz, CH=). MS (m/z): 317(M+, 45), 302(M+-15, 3), 272(M+-45, 5), 202(M+-115, 90). Anal. Cald. for C22H31N2O5Cl: C:61.10%, H:6.78%, N: 3.96%; Found: C: 61.23%, H:6.59%, N:3.98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; at 20.0℃; | A mixture of 1-(6-[4-ethyl-5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]amino}pyrimidin-4-yl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid (72.6 mg, 167 μιηο), cis-<strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> (1 : 1) (50.6 mg, 333 μιηο), (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) (139 mg, 367 μιηο) and N,N-Diisopropylethylamine (120 μ, 700 μηιο) was stirred overnight at room temperature. The mixture was directly purified by preparative HPLC (method: column: Reprosil C18; 10 μηι; 125x30 mm / flow: 50 ml/min / eluent: A = water (0.01% formic acid), B = acetonitrile / gradient: 0.00-5.00 min = 10% B, 6.50 min = 20% B, 17.0-19.75 min = 100% B, 19.75-23.00 min = 90% B) to yield 49.8 mg (56% yield) of the desired product. LC-MS (method 10): Rt = 1.99 min; MS (ESIpos): m/z = 533 [M+H]+1H-NMR (400 MHz, DMSO-d6) δ [ppm]: -0.008 (4.17), 0.008 (2.94), 0.146 (0.41), 0.871 (3.38), 0.890 (7.62), 0.909 (3.51), 1.073 (3.40), 1.091 (5.53), 1.108 (3.43), 2.165 (5.64), 2.286 (0.76), 2.304 (2.17), 2.323 (2.61), 2.366 (0.41), 2.523 (2.02), 2.670 (0.70), 2.710 (0.49), 3.357 (0.82), 3.375 (2.25), 3.392 (2.26), 3.410 (0.95), 3.478 (0.89), 3.651 (16.00), 7.359 (2.06), 7.381 (6.32), 7.403 (2.69), 7.499 (2.50), 7.512 (2.88), 7.520 (2.17), 7.534 (1.85), 8.477 (3.59), 9.433 (2.07). |
A339625 [168038-14-0]
(R)-2-Methylmorpholine hydrochloride
Similarity: 1.00
A267107 [276252-76-7]
(2S,6S)-2,6-Dimethylmorpholine hydrochloride
Similarity: 1.00
A729984 [N/A]
(2R,6R)-2,6-Dimethylmorpholine hydrochloride
Similarity: 1.00
A502948 [1147108-99-3]
(S)-2-Methylmorpholine hydrochloride
Similarity: 1.00
A502948 [1147108-99-3]
(S)-2-Methylmorpholine hydrochloride
Similarity: 1.00