Amantadine → HCID 70622003, compound

HRID 616489Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:19][C:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>>[ClH:12].[C:20]12([NH:19][CH2:2][CH2:3][CH2:4][S:5][C:6]3[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=3[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:27][CH:26]3[CH2:25][CH:24]([CH2:23][CH:22]([CH2:28]3)[CH2:21]1)[CH2:29]2

Participants

Reactant 2

HCID 2130Amantadine

HCID 20367395HCID 20367395, compound

Product 1

HCID 70622003HCID 70622003, compound

Procedure

A mixture of 15 g. of 2-(3-bromopropylthio)-5-chlorobiphenyl and an excess of 1-aminoadamantane was heated in an oil bath at about 120° C. for about 4 hours. The reaction mixture was worked up and the product was isolated as the hydrochloride acid addition salt in the manner described in previous examples. The product had a melting point of about 304°-305° C., and was identified as N-adamantyl-3-(5-chloro-2-biphenylylthio)propylamine hydrochloride.

Workup

additionA mixture of 15 g

Sources & evidence

ORD record: ord-d7259b28f555439e899b0af445fe2418
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04074998

Reaction notes

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