Benzoyl chloride, 3-chloro- → 4-(3-Chloro-benzoyl)-2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester

HRID 334022Notes

Reaction equation

HRID 334022 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1([CH3:25])[CH3:24])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(C(C)C)C(C)C.[Cl:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=1)[C:39](Cl)=[O:40]>CCOC(C)=O>[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:39](=[O:40])[C:38]2[CH:42]=[CH:43][CH:44]=[C:36]([Cl:35])[CH:37]=2)[CH2:20][C:19]1([CH3:25])[CH3:24])=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-HCID 81531DiisopropylethylamineHCID 866882432,2-Dimethyl-piperazine-1-carboxylic acid benzyl ester trifluoroacetate

Product 1

HCID 866882534-(3-Chloro-benzoyl)-2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.00 g (8.28 mmol) 2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester trifluoroacetate in 50 mL EtOAc was added 3.50 mL (20.3 mmol) DIPEA followed by 1.07 mL (8.28 mmol) 3-chloro-benzoyl chloride dropwise at RT. The reaction mixture was stirred at RT for 1 h. Then the suspension was washed with water. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo.

Workup

  1. washThen the suspension was washed with water
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e1b24cbfc6143699900dc94895aa397
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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