1-Chloroethyl chloroformate → 1-(Benzothiophen-2-yl)piperazine hydrochloride

HRID 1900560Notes

Reaction equation

HRID 1900560 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[CH:18]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:23]C(OC(Cl)=O)C>ClCCl>[ClH:23].[S:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[CH:18]=[C:14]1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 217016231-Benzyl-4-(benzothiophen-2-yl)piperazine

Product 1

HCID 190649731-(Benzothiophen-2-yl)piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-4-(benzothiophen-2-yl)piperazine (1.5 g, 4.9 mmol) in anhydrous dichloromethane (20 ml) at 0° C. under nitrogen was added 1-chloroethylchloroformate (0.68 ml, 6.37 mmol). The mixture was allowed to warm to room temperature, stirred for 1 h and concentrated in vacuo. The crude residue was dissolved in methanol (10 ml) and heated to reflux for 30 minutes, left to cool and the title compound collected by filtration (0.6 g), m.p. 240° C. (dec.).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude residue was dissolved in methanol (10 ml)
  3. temperatureheated
  4. temperatureto reflux for 30 minutes
  5. waitleft
  6. temperatureto cool
  7. filtrationthe title compound collected by filtration (0.6 g), m.p. 240° C. (dec.)

Sources & evidence

ORD record
ord-67a08c733cb949368f22a3192202c0ff
Source dataset
uspto-grants-1996_11
Patent number
US05576319

Reaction notes

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