Hydrochloric Acid → [2-(2-Benzenesulfonyl-1H-indol-7-yloxy)-ethyl]-methyl-amine hydrochloride

HRID 6954Notes

Reaction equation

C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[O:17][CH2:18][CH2:19][N:20](C(OC(C)(C)C)=O)[CH3:21])[CH:10]=[C:9]1[S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])=[O:30])=O)(C)(C)C.[ClH:38]>CCO>[ClH:38].[C:32]1([S:29]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH2:18][CH2:19][NH:20][CH3:21])(=[O:31])=[O:30])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Benzenesulfonyl-7-[2-(tert-butoxycarbonyl-methyl-amino)-ethoxy]-indole-1-carboxylic acid tert-butyl ester (0.230 g., 0.43 mmol) from the above step was dissolved in 5 mL EtOH. To this solution was added 1 mL of 2M ethanolic hydrogen chloride solution. The reaction mixture was heated at 100° C. for 35 minutes. Upon cooling to ambient temperature, a fine white precipitate was observed. After filtration and drying in vacuo at 60° C., [2-(2-Benzenesulfonyl-1H-indol-7-yloxy)-ethyl]-methyl-amine hydrochloride was obtained as 0.140 g. white crystals. MS: 329 (M−H)−, mp=289.4–291.6° C.

Workup

temperatureUpon cooling to ambient temperature
filtrationAfter filtration
customdrying in vacuo at 60° C.

Sources & evidence

ORD record: ord-97136cb279ec42c48c1676e51c7624a8
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084169B2

Reaction notes

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