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

HRID 8339Notes

Reaction equation

HRID 8339 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.C(Cl)[Cl:35]>>[ClH:35].[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

3

Reactant 2

HCID 6344DichloromethaneHCID 22015348n-(4-Methoxybenzenesulfonyl)-5-(4-benzylpiperazin-1-yl)-indole

Product 1

HCID 69049332n-(4-Methoxybenzenesulfonyl)-5-(piperazin-1-yl)-indole, hydrochloride

Procedure

N-(4-Methoxybenzenesulfonyl)-5-(4-benzylpiperazin-1-yl)-indole (0.25 g, 0.54 mmol) was dissolved in DCM (4 mL), a-chloroethyl chlorofonnate (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 (8 H, m), 3.77 (3 H, s), 6.64 (1 H, d, J=3), 6.94 (2 H, d, J=9), 7.15 (1 H, dd, J=9, 2), 7.26 (1 H, d, J=2), 7.59 (1 H, d, J=4), 7.80 (2 H, d, J=9) and 7.90 (1 H, d, J=9); MS (posES-FIA) 371.1304 M+; Purity (HPLC chromsil C18) >98%. Examples 89–95 were prepared using the same procedure as in example 88.

Workup

  1. additiona-chloroethyl chlorofonnate (0.150 g, 1.05 mmol) was added
  2. concentrationwas concentrated
  3. additionMeOH (10 mL) was added
  4. temperaturethe mixture refluxed for 2 hrs
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6b2a56a0275840ea9924f474c1ec4f3d
Source dataset
uspto-grants-2006_08
Patent number
US07087750B2

Reaction notes

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