Dichloromethane → Biphenyl-2-ylcarbamic acid 1-[2-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenylcarbamoyl)ethyl]piperidin-4-yl ester

HRID 1361730Notes

Reaction equation

HRID 1361730 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8](=[O:22])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][CH2:2]1.[O:23]1[CH2:27][CH2:26][O:25][CH:24]1[C:28]1[C:33]([CH3:34])=[CH:32][C:31]([NH:35][C:36](=[O:39])[CH:37]=[CH2:38])=[C:30]([CH3:40])[CH:29]=1.ClCCl>C(O)C>[O:23]1[CH2:27][CH2:26][O:25][CH:24]1[C:28]1[C:33]([CH3:34])=[CH:32][C:31]([NH:35][C:36]([CH2:37][CH2:38][N:1]2[CH2:2][CH2:3][CH:4]([O:7][C:8](=[O:22])[NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:5][CH2:6]2)=[O:39])=[C:30]([CH3:40])[CH:29]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl EsterHCID 57461077N-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenyl)acrylamide

Product 1

HCID 46239623Biphenyl-2-ylcarbamic acid 1-[2-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenylcarbamoyl)ethyl]piperidin-4-yl esterYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a 500 mL round-bottom flask was added biphenyl-2-ylcarbamic acid piperidin-4-yl ester (17.0 g, 58 mmol) and N-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenyl)acrylamide (13.1 g, 52.9 mmol). Ethanol (150 mL) and dichloromethane (150 mL) were added to form a slurry. The reaction mixture was heated at 50° C. to 55° C. for about 24 hours and then cooled to room temperature. Most of the solvent was removed on a rotary evaporator, resulting in a thick slurry. Ethanol (reagent grade) was added to form a total volume of about 200 mL and the resulting mixture was heated to 80° C. and then cooled slowly to room temperature. The resulting thick white slurry was filtered, washed with ethanol (20 mL) and dried in vacuum to provide biphenyl-2-ylcarbamic acid 1-[2-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenylcarbamoyl)ethyl]piperidin-4-yl ester (23.8 g, about 98% purity) as a white solid.

Workup

  1. customto form a slurry
  2. temperatureThe reaction mixture was heated at 50° C. to 55° C. for about 24 hours
  3. customMost of the solvent was removed on a rotary evaporator
  4. customresulting in a thick slurry
  5. customto form a total volume of about 200 mL
  6. temperaturethe resulting mixture was heated to 80° C.
  7. temperaturecooled slowly to room temperature
  8. filtrationThe resulting thick white slurry was filtered
  9. washwashed with ethanol (20 mL)
  10. customdried in vacuum

Sources & evidence

ORD record
ord-2735869244744d1592bd1d1788d05533
Source dataset
uspto-grants-2011_02
Patent number
US07880010B2

Reaction notes

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