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

HRID 1888878Notes

Reaction equation

HRID 1888878 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-5ca0efaffe06471b9bff3f510f0b776f
Source dataset
uspto-grants-2013_08
Patent number
US08501774B2

Reaction notes

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