tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate → Tert-butyl 4-(6-{2-[4-(2-hydroxyethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate

HRID 1465502Notes

Reaction equation

HRID 1465502 reaction equation
[Br-].[OH:2][CH2:3][CH2:4][C:5]1[CH:30]=[CH:29][C:8]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][CH:6]=1.[CH:31]([C:33]1[N:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]2)=[CH:35][CH:34]=1)=O>>[OH:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:9]=[CH:31][C:33]2[N:38]=[CH:37][C:36]([N:39]3[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]3)=[CH:35][CH:34]=2)=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 58181229tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylateHCID 86651852[4-(2-Hydroxyethyl)benzyl](triphenyl)phosphonium bromide

Product 1

HCID 67030871Tert-butyl 4-(6-{2-[4-(2-hydroxyethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate

Procedure

By a method similar to Production Example 108, step 4, [4-(2-hydroxyethyl)benzyl](triphenyl)phosphonium bromide (2.866 g, 6.004 mmol) and tert-butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate (1.458 g, 5.003 mmol) were condensed to give tert-butyl 4-(6-{2-[4-(2-hydroxyethyl)phenyl]vinyl}pyridin-3-yl)piperazine-1-carboxylate (5.684 g, quantitatively) as a colorless oil.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-fe63024ada0b4642be902139a1423100
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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