Isopropanol → 1-(3'-Chloropropyl)-1,2,3,4-tetrahydro-beta-carboline hydrochloride

HRID 1285199Notes

Reaction equation

[Cl:1]CCCC=O.[Cl:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=O.Cl.[NH2:15][CH2:16][CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1.C(O)(C)C>C1(C)C(C)=CC=CC=1>[ClH:1].[Cl:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:19]2[NH:20][C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]=2[CH2:17][CH2:16][NH:15]1

Participants

Conditions

Temperature: 88 °C

Procedure

1,280 parts of a 20.7% strength by weight solution of γ-chlorobutyraldehyde in xylene (prepared by a method similar to that described in Houben-Weyl, Volume 7/1, pages 285-290, by catalytic hydrogenation of a solution of γ-chlorobutyric acid chloride in xylene), 490 parts of 3-(β-aminoethyl)-indole hydrochloride and 1,000 parts of isopropanol were stirred for 4 hours at 88° C., and the mixture was cooled and then filtered under suction to give 618 parts (87%) of 1-(γ-chloropropyl)-1,2,3,4-tetrahydro-β-carboline hydrochloride. After recrystallization from methanol, the substance had a melting point of 219°-221° C.

Workup

temperaturethe mixture was cooled
filtrationfiltered under suction

Sources & evidence

ORD record: ord-fc11bb30c8e44d4888489ad31c21d813
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04565870

Reaction notes

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