Cesium carbonate → 4-[2-(2,4-Bis-benzyloxy-5-chloro-phenyl)-2-oxo-ethyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1433139Notes

Reaction equation

HRID 1433139 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:14][C:15]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]([Cl:29])=[CH:17][C:16]=1[C:30](=[O:33])[CH2:31]Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>CN(C)C=O>[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][N:44]([CH2:31][C:30]([C:16]2[CH:17]=[C:18]([Cl:29])[C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][C:15]=2[O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:33])[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 579348271-(2,4-Bis-benzyloxy-5-chloro-phenyl)-2-bromo-ethanone

Product 1

HCID 690632014-[2-(2,4-Bis-benzyloxy-5-chloro-phenyl)-2-oxo-ethyl]-piperazine-1-carboxylic acid tert-butyl esterYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (2.95 g, 9 mmol) was added in three portions to a stirred solution of 1-(2,4-Bis-benzyloxy-5-chloro-phenyl)-2-bromo-ethanone (4.4 g, 9 mmol) and piperazine-1-carboxylic acid tert-butyl ester (1.74 g, 9 mmol) in dimethylformamide (20 ml). The suspension was stirred for 2 h then partitioned between water (200 ml) and ethyl acetate (3×50 ml). The combined organic extracts were washed with water (100 ml), dried over magnesium sulphate and concentrated to give 4-[2-(2,4-Bis-benzyloxy-5-chloro-phenyl)-2-oxo-ethyl]-piperazine-1-carboxylic acid tert-butyl ester as a yellow oil (4 g)

Workup

  1. customthen partitioned between water (200 ml) and ethyl acetate (3×50 ml)
  2. washThe combined organic extracts were washed with water (100 ml)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-112d0846dfe04a2da9cbbfc042c73035
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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