Triethylamine → Tert-butyl 4-(2-fluorobenzoyl)piperazine-1-carboxylate

HRID 729615Notes

Reaction equation

HRID 729615 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[F:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 4863006Tert-butyl 4-(2-fluorobenzoyl)piperazine-1-carboxylateYield 104.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperazine-1-carboxylic acid tert-butyl ester (10 g, 53.7 mmol) in dichloromethane (300 mL), add triethyl amine (15.1 mL, 107.4 mmol) and 2-fluorobenzoyl chloride (6.4 mL, 53.7 mmol). Stir the mixture at room temperature overnight. Then add water (200 mL) and separate the organic layer, dry over sodium sulfate, filter and evaporate solvent under reduced pressure to give 17.3 g of 4-(2-fluoro-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester. ES+ (m/z) 309[M+H].

Workup

  1. customThen add water (200 mL) and separate the organic layer
  2. dry with materialdry over sodium sulfate
  3. filtrationfilter
  4. customevaporate solvent under reduced pressure

Sources & evidence

ORD record
ord-6cc1a319048d422489a7669d259f6ff3
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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