1-(Pyridin-4-yl)piperidin-4-one → (3S)-3-(tert-butoxycarbonylamino)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-pyrrolidone

HRID 2086253Notes

Reaction equation

HRID 2086253 reaction equation
[NH2:1][N:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:3]1=[O:15].[N:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C(O)C>[C:11]([O:10][C:8]([NH:7][C@H:4]1[CH2:5][CH2:6][N:2]([N:1]=[C:25]2[CH2:24][CH2:23][N:22]([C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)[CH2:27][CH2:26]2)[C:3]1=[O:15])=[O:9])([CH3:12])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 113327931-(Pyridin-4-yl)piperidin-4-oneHCID 45092234(S)-tert-Butyl (1-amino-2-oxopyrrolidin-3-yl)carbamate

Product 1

HCID 69545990(3S)-3-(tert-butoxycarbonylamino)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-pyrrolidoneYield 111.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (3S)-1-amino-3-(tert-butoxycarbonylamino)-2-pyrrolidone (1.84 g) and 1-(4-pyridyl)-4-piperidone (1.51 g) in ethanol (30 ml) was dehydrated using a Soxlet extractor packed with molecular sieves 4A while refluxing for 15 hours. The reaction mixture was concentrated to obtain (3S)-3-(tert-butoxycarbonylamino)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-pyrrolidone (3.57 g) as a syrup.

Workup

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

Sources & evidence

ORD record
ord-1c5851ad671f4ecf927a6ace9a2874c1
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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