Phenol, 4-amino-, 1-acetate → 4-(4-Acetoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726178Notes

Reaction equation

HRID 1726178 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=1>>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23](=[O:25])[CH3:24])=[CH:20][CH:21]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

3

Reactant 2

HCID 83783Phenol, 4-amino-, 1-acetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 689735994-(4-Acetoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl esterYield 80.5%

Procedure

Using general procedure A, 1-Boc-4-piperidone (2.52 g, 12.66 mmol) and acetic acid 4-amino-phenyl ester (Bargota, Rakesh S.; et al., Bioorg. Med. Chem. Lett., 13, 10, 2003, 1623-1626) (2.95 g, 19.52 mmol) afforded 4-(4-acetoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester as a white solid (3.41 g, 76%).

Sources & evidence

ORD record
ord-401cff06404c44eb9b448528b057b2b1
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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