1-Chloroethyl chloroformate → 1-(3,5-Dichloro-benzenesulfonyl)-4-piperazin-1-yl-1H-indole

HRID 1006418

Reaction equation

HRID 1006418 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[S:23]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)(=[O:25])=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[Cl:32][C:30]1[CH:31]=[C:26]([S:23]([N:18]2[C:19]3[C:15](=[C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:22]=[CH:21][CH:20]=3)[CH:16]=[CH:17]2)(=[O:25])=[O:24])[CH:27]=[C:28]([Cl:33])[CH:29]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 121371244-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole

Product 1

HCID 102232611-(3,5-Dichloro-benzenesulfonyl)-4-piperazin-1-yl-1H-indole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 0.1 g (0.2 mmole) 4-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole and 0.05 mL (0.46 mmole) 1-chloroethyl chloroformate in 10 mL 1,2-dichloroethane was heated under reflux for 0.5 hour. The solution was concentrated under reduced pressure and the residue was dissolved in 6 mL methanol. The solution was heated under reflux for 1 hour, then it was concentrated. 1-(3,5-Dichloro-benzenesulfonyl)-4-piperazin-1-yl-1H-indole (2) was isolated as the hydrochloride salt from methanol/ethyl ether, 74 mg, M+H=410, m.p. 156-157° C.

Workup

  1. temperatureunder reflux for 0.5 hour
  2. concentrationThe solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 6 mL methanol
  4. temperatureThe solution was heated
  5. temperatureunder reflux for 1 hour
  6. concentrationit was concentrated

Sources & evidence

ORD record
ord-25b87b6c49774dbea738442a5ddde63f
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Linked notes

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