Bromoacetyl bromide → tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylate

HRID 2279682Notes

Reaction equation

HRID 2279682 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(C(C)C)CC)(C)C>ClCCl>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:3](=[O:4])[CH2:2][Br:1])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylateYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromo acetyl bromide (4.86 ml, 21.47 mmol, 1 eq) was added dropwise to a stirred ice cold mixture of the piperazine-1-carboxylic acid tert butyl ester (4.0 g, 21.47 mmol, 1 eq) and diisopropyl ethyl amine (12.05 g, 92.5 mmol, 4.3 eq) in dichloromethane (108 ml). The resulting mixture was washed with water (2×50 mL) and saturated sodium chloride solution (100 mL), and dried over MgSO4. After filtration, the solvent was evaporated and the residue was purified with chromatography with (ethyl acetate/n-hexane 1/1) to give the product (2.72 g, 41%) as a orange oil.

Workup

  1. washThe resulting mixture was washed with water (2×50 mL) and saturated sodium chloride solution (100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. customthe solvent was evaporated
  5. customthe residue was purified with chromatography with (ethyl acetate/n-hexane 1/1)

Sources & evidence

ORD record
ord-54553a0a6ff44881a80193d17ef6f3c0
Source dataset
uspto-grants-2015_09
Patent number
US09133213B2

Reaction notes

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