1-Chloroethyl chloroformate → n-(4-Methoxybenzenesulfonyl)-5-(piperazin-1-yl)-indole, hydrochloride

HRID 2112465Notes

Reaction equation

HRID 2112465 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([N:21]4[CH2:26][CH2:25][N:24](CC5C=CC=CC=5)[CH2:23][CH2:22]4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Cl:34]C(OC(Cl)C)=O>C(Cl)Cl>[ClH:34].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 22015348n-(4-Methoxybenzenesulfonyl)-5-(4-benzylpiperazin-1-yl)-indole

Product 1

HCID 69049332n-(4-Methoxybenzenesulfonyl)-5-(piperazin-1-yl)-indole, hydrochlorideYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Methoxybenzenesulfonyl)-5-(4-benzylpiperazin-1-yl)-indole (0.25 g, 0.54 mmol) was dissolved in DCM (4 mL), α-chloroethyl chloroformate (0.150 g, 1.05 mmol) was added and the mixture left at room temperature for 2 h after which it was concentrated. MeOH (10 mL) was added and the mixture refluxed for 2 hrs and then concentrated to give the product (0.22 g, quantitative yield). 1H NMR (MeOH d6) δ 3.39-3.47 (8H, m), 3.77 (3H, s), 6.64 (1H, d, J=3), 6.94 (2H, d, J=9), 7.15 (1H, dd, J=9, 2), 7.26 (1H, d, J=2), 7.59 (1H, d, J=4), 7.80 (2H, d, J=9) and 7.90 (1, H, d, J=9); MS (posES-FIA) 371.1304 M+; Purity (HPLC chromsil C18) >98%.

Workup

  1. concentrationwas concentrated
  2. additionMeOH (10 mL) was added
  3. temperaturethe mixture refluxed for 2 hrs
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e86a32a566da4a88b2ccfe24aa6746aa
Source dataset
uspto-grants-2009_04
Patent number
US07524839B2

Reaction notes

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