Triethylamine → tert-Butyl 4-[(3-bromophenyl)methyl]piperazine-1-carboxylate

HRID 2065510Notes

Reaction equation

HRID 2065510 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.C(N(CC)CC)C.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][N:20]1[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 699793-Bromobenzyl bromideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 53439212tert-Butyl 4-[(3-bromophenyl)methyl]piperazine-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-bromo-3-(bromomethyl)benzene (677 mg, 2.71 mmol) in THF (10 ml) was added triethylamine (380 μL, 2.71 mmol), followed by tert-butyl piperazine-1-carboxylate (504 mg, 2.71 mmol). The mixture was allowed to stir at RT for one hour. The solvent was evaporated and the residue was purified with a silica gel column eluting with 1:10 EtOAc/hexanes to give the title compound as an oil (888 mg, 2.49 mmol, 92%). [M+H] calc'd for C16H24BrN2O2, 355; found, 355.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified with a silica gel column
  3. washeluting with 1:10 EtOAc/hexanes

Sources & evidence

ORD record
ord-a5bf4ceac0c7441eaf014e8c4d9c5bfb
Source dataset
uspto-grants-2012_10
Patent number
US08288536B2

Reaction notes

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