3-tert-Butylaniline → 4-[4-(3-Tert-butyl-phenylcarbamoyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 2190646Notes

Reaction equation

HRID 2190646 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:23]([C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30])([CH3:26])([CH3:25])[CH3:24].C(OC(N1CCN(C2C=CC(C(=O)NC3C=CC=C(C(C)(C)C)C=3)=CC=2)CC1)=O)(C)(C)C>>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:28]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 3

HCID 793343-tert-ButylanilineHCID 224928594-(4-Carboxy-phenyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 593180174-[4-(3-Tert-butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 593180124-[4-(3-Tert-butyl-phenylcarbamoyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Procedure

4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester was prepared from N-Boc-4-(4-carboxyphenyl)piperidine and 3-tert-butyl aniline in a manner similar to the one described in the synthesis of 4-[4-(3-tert-butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester, above. The product was isolated after silica gel column purification with 10-50% Et2O in hexanes. HRMS m/z calcd for C26H35N3O3I [M+H]+: 437.2799. Found: 437.2796.

Workup

  1. customThe product was isolated
  2. customafter silica gel column purification with 10-50% Et2O in hexanes

Sources & evidence

ORD record
ord-1b6bd83124dd4b63bff78455220d2a14
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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