tert-Butyl 4-oxopiperidine-1-carboxylate → 4-Benzyloxycarbonyl-1-[1-(tert-butoxycarbonyl)-4-piperidinylideneamino]-2-piperazinone

HRID 2086230Notes

Reaction equation

HRID 2086230 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][C:3]1=[O:18].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C(O)C>[CH2:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][N:2]([N:1]=[C:29]2[CH2:30][CH2:31][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH2:27][CH2:28]2)[C:3](=[O:18])[CH2:4]1)=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 22727156Benzyl 4-amino-3-oxopiperazine-1-carboxylate

Product 1

HCID 227272314-Benzyloxycarbonyl-1-[1-(tert-butoxycarbonyl)-4-piperidinylideneamino]-2-piperazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-amino-4-benzyloxycarbonyl-2-piperazinone (2.49 g) and 1-(tert-butoxycarbonyl)-4-piperidone (1.99 g) in ethanol (40 ml) was dehydrated using a Soxlet extractor packed with molecular sieves 4A while refluxing for 15 hours. The reaction mixture was concentrated to obtain a crude 4-benzyloxycarbonyl-1-[1-(tert-butoxycarbonyl)-4-piperidinylideneamino]-2-piperazinone as an oil.

Workup

  1. temperaturewhile refluxing for 15 hours
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-6f266f2f3c69477a929d781ee8aac2b7
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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