Triethylamine → Benzyl 4-(4-bromophenyl)piperazine-1-carboxylate

HRID 41693

Reaction equation

HRID 41693 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>ClCCl>[CH2:25]([O:24][C:22]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 27356291-(4-Bromophenyl)piperazine

Product 1

HCID 46739494Benzyl 4-(4-bromophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g of 4-bromophenylpiperazine are placed in a 500 ml three-necked flask under a nitrogen atmosphere. 4.34 ml of triethylamine are added. The mixture is cooled in an ice bath and 3.24 ml of benzyl chloroformate are added. The mixture is allowed to return to ambient temperature. It is diluted with dichloromethane and then gentle hydrolysis is carried out. The aqueous phase is extracted with dichloromethane. The organic phases are combined, washed with a saturated NaCl solution, dried over sodium sulphate, then filtered through a sintered glass filter and concentrated under vacuum. 8.43 g of 4-(4-bromophenyl)piperazine-1-carboxylic acid benzyl ester are obtained.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. customto return to ambient temperature
  3. customgentle hydrolysis
  4. extractionThe aqueous phase is extracted with dichloromethane
  5. washwashed with a saturated NaCl solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered through a sintered glass
  8. filtrationfilter
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c53fbf5f16654f649222fece5a7bfb47
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Linked notes

Loading…