O-p-Chlorophenyl chlorothioformate → 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)ester

HRID 49510Notes

Reaction equation

HRID 49510 reaction equation
[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH2:15][CH2:14]2)[CH3:5])[CH:2]=[CH2:3].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28](Cl)=[S:29])=[CH:23][CH:22]=1>O1CCOCC1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][N:4]([CH2:1][CH:2]=[CH2:3])[CH3:5])=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)=[S:29])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 70306O-p-Chlorophenyl chlorothioformateHCID 21966638Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine

Product 1

HCID 99543375-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)esterYield 42.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

130 mg (0.5 mmol) Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine in 0.5 ml dioxane were treated with 0.072 ml (0.5 mmol) chlorothio-formicacid-O-(4-chlorophenyl)-ester at 15° C. The mixture was stirred for 15 min, concentrated and purified by column chromatography on silica gel with a gradient of CH2Cl2MeOH 99:1 to 97:3 to yield 92 mg 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)ester as colorless oil. The corresponding acetic acid salt was prepared by treatment with acetic acid in CH2Cl2 to yield 101 mg 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carbothioic acid O-(4-chloro-phenyl)esteracetic acid as light brown viscous oil, MS: 429 (MH+, 1Cl).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography on silica gel with a gradient of CH2Cl2MeOH 99:1 to 97:3

Sources & evidence

ORD record
ord-c9a983a38d4e469484daefd6df09f929
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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