2-Piperidone → benzyl 4-((N-(4-cyanophenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate

HRID 1596674Notes

Reaction equation

HRID 1596674 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.N1CCCCC1=O.CS(C)(=O)=C.[NH2:31][C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=1>>[C:36]([C:35]1[CH:38]=[CH:39][C:32]([NH:31][CH2:2][C:3]2([OH:1])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)=[CH:33][CH:34]=1)#[N:37]

Participants

5

Reactant 4

HCID 126652-PiperidoneHCID 133964-AminobenzonitrileHCID 6396768Dimethylsulfoxonium methylideHCID 13016598Benzyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Product 1

HCID 23435775benzyl 4-((N-(4-cyanophenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate

Procedure

A mixture of 20.0 g (80.9 mmol) benzyl 1-oxa-6-aza-spiro[2.5]octane-6-carboxylate (prepared from the protected piperidone and dimethylsulfoxonium methylide according to J. Med. Chem. 1983, 26, 855; U.S. Pat. No. 4,353,901) and 47.0 g (397.8 mmol) 4-aminobenzonitrile were heated at 160° C. for 30 hours until no starting epoxide could be detected by TLC. It was cooled to room temperature, and the excess of the aniline was removed by chromatography on silica gel with dichloromethane. The title compound was obtained after enhancing the polarity of the eluent by addition of 5% ethanol.

Workup

  1. customthe excess of the aniline was removed by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-42ae2dd487d24bf0ba85a724d4e651d5
Source dataset
uspto-grants-2001_09
Patent number
US06291469B1

Reaction notes

Loading…