Water → HCID 86674535, compound

HRID 1615406Notes

Reaction equation

HRID 1615406 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[C:11]([O:15][C:16](=[O:30])[C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.O>C(#N)C.CC(N(C)C)=O>[C:11]([O:15][C:16](=[O:30])[C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:24][CH2:25][CH:26]([NH:29][C:2]([O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:3])[CH2:27][CH2:28]2)=[CH:19][CH:18]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 22557720HCID 22557720, compound

Product 1

HCID 86674535HCID 86674535, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

Phenyl chloroformate (7.83 g, 50.0 mmol) was dissolved in acetonitrile (100 ml), and a solution of the 4-(4-aminopiperidin-1-yl)-benzoic acid tert-butyl ester (13.82 g, 50.0 mmol) obtained in Example 1(1) in acetonitrile (50 ml) and DMA (50 ml) was added dropwise under ice-cooling. Triethylamine (7.0 ml, 50.0 mmol) was added thereto. After stirring at the same temperature for 2 hours, water was added thereto, and the precipitate was collected by filtration, thereby obtaining 4-(4-phenoxycarbonylaminopiperidin-1-yl)-benzoic acid tert-butyl ester (15.5 g, 78%) as a milky-white solid. The obtained 4-(4-phenoxycarbonylaminopiperidin-1-yl)-benzoic acid tert-butyl ester was used as is in the next reaction.

Workup

  1. temperaturecooling
  2. filtrationthe precipitate was collected by filtration
  3. customas is in the next reaction

Sources & evidence

ORD record
ord-7245ca399a6f4c0cb18b36232efddb3e
Source dataset
uspto-grants-2014_07
Patent number
US08765750B2

Reaction notes

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