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

HRID 421834Notes

Reaction equation

HRID 421834 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].C(Cl)(Cl)Cl.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C(OCC)(=O)C>[Br:1][CH2:2][C:3]([N:20]1[CH2:19][CH2:18][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:22][CH2:21]1)=[O:4]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

With cooling with ice, bromoacetyl bromide (680 μL) was added to a chloroform (10 ml) solution of 1-tert-butyloxycarbonylpiperazine (1 g) and triethylamine (2.2 mL). At that temperature, this was stirred for 0.5 hours, and then at room temperature for further 0.5 hours. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=7/3) to obtain 340 mg of the entitled compound.

Workup

  1. waitat room temperature for further 0.5 hours
  2. customThe reaction liquid
  3. washwashed with water and saturated saline water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-416098bc7ea845c8b9890c1bae4291e0
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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