Rac-4-(2-amino-1-phenyl-ethyl)-1-benzyl-piperidine-4-carboxylic acid ethyl ester → Rac-8-benzyl-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one

HRID 914932Notes

Reaction equation

HRID 914932 reaction equation
C([O:3][C:4]([C:6]1([CH:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][NH2:21])[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=O)C>C1(C)C=CC=CC=1>[CH2:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:3])[NH:21][CH2:20][CH:19]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:7][CH2:8]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 66918079Rac-4-(2-amino-1-phenyl-ethyl)-1-benzyl-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 21082592Rac-8-benzyl-4-phenyl-2,8-diaza-spiro[4.5]decan-1-oneYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of rac-4-(2-amino-1-phenyl-ethyl)-1-benzyl-piperidine-4-carboxylic acid ethyl ester (2.9 g, 8 mmol) in toluene (30 mL) was heated under reflux for 4 h. After cooling to room temperature and evaporation the mixture was purified by chromatography on silica gel eluting with DCM:MeOH:NH4OH (95:4.5:0.5) to afford the title compound (1.47 g, 58%) as a white solid. MS: m/e=321.4 (M+H).

Workup

  1. temperatureunder reflux for 4 h
  2. customevaporation the mixture
  3. customwas purified by chromatography on silica gel eluting with DCM:MeOH:NH4OH (95:4.5:0.5)

Sources & evidence

ORD record
ord-d913335e8c4a4abcb06486c5bee74992
Source dataset
uspto-grants-2007_09
Patent number
US07265126B2

Reaction notes

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