Phosgene → 4-(1-benzyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 730556Notes

Reaction equation

HRID 730556 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]=2[NH2:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29](=O)([O-])[O-:30].[Na+].[Na+].C(Cl)(Cl)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[NH:28][C:29](=[O:30])[N:20]([CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:16]=3[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 10340Sodium CarbonateHCID 578349834-(2-Amino-3-benzylamino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 578349934-(1-benzyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-amino-3-benzylamino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.176 g, 0.459 mmol) in 1 mL dichloromethane was added 1 mL of 2M aqueous sodium carbonate. Phosgene (0.261 mL of a 1.93 M solution in toleuene, 0.504 mmol) was added dropwise to the stirring solution over five minutes. Stirring was continued for two hours as a fine white precipitate was formed. The solid was filtered and dried under a stream of nitrogen to give 0.112 g of 4-(1-benzyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester as a fine white powder. MS: 409 (M+H)+.

Workup

  1. customwas formed
  2. filtrationThe solid was filtered
  3. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-17b2729ed8284301afbd9f41bc549ea1
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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