Biphenyl-2-ylcarbamic Acid Piperidin-4-yl Ester → 3-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)benzoic Acid Methyl Ester

HRID 1039846Notes

Reaction equation

HRID 1039846 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][C:12](=[O:15])[CH:13]=[CH2:14])[CH:5]=1.[NH:17]1[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:38])[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:19][CH2:18]1>CCO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][C:12](=[O:15])[CH2:13][CH2:14][N:17]2[CH2:18][CH2:19][CH:20]([O:23][C:24](=[O:38])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:21][CH2:22]2)[CH:5]=1

Participants

4

Reactant 2

HCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl EsterHCID 667703313-(Acryloylmethylamino)benzoic Acid Methyl Ester

Product 1

HCID 667815453-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)benzoic Acid Methyl EsterYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 3-(acryloylmethylamino)benzoic acid methyl ester (estimated ˜56 mmol) and biphenyl-2-ylcarbamic acid piperidin-4-yl ester (16.6 g, 56.0 mmol) in EtOH (20.0 mL) was heated at 90° C. overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel flash chromatography (0-10% MeOH in DCM) to give the title compound (13.0 g, 45% yield) as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel flash chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-6ffcb77001654cc4a2ee932e21659541
Source dataset
uspto-grants-2013_10
Patent number
US08551978B2

Reaction notes

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