Triethylamine → tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylate

HRID 898809Notes

Reaction equation

HRID 898809 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[C:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.O>[C:6]([N:13]1[CH2:14][CH2:15][N:16]([C:3](=[O:4])[CH2:2][Br:1])[CH2:17][CH2:18]1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylateYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of bromoacetyl bromide (29.8 g, 148 mmol) in THF (250 mL) at 0° C. was added via an addition funnel a solution of Boc-piperazine (25 g, 134 mmol) and triethylamine (14.9 g, 148 mmol) in THF (75 mL). After 1 h, a few grams of ice were added and the mixture was diluted with ethyl acetate and cold water. The layers were separated and the organic phase was washed with 1 M aq. citric acid, brine, satd aq. NaHCO3 and again with brine. The organic phase was then dried with MgSO4, filtered, and concentrated in vacuo to give 38.2 g (93%) of an off-white powder.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed with 1 M aq. citric acid, brine
  3. dry with materialThe organic phase was then dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-644f7e725ca94310b7dbccc8f3c43dff
Source dataset
uspto-grants-2008_04
Patent number
US07351822B2

Reaction notes

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