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

HRID 1285202Notes

Reaction equation

HRID 1285202 reaction equation
C(O[CH:4](OCC)[CH2:5][CH2:6][CH2:7][Cl:8])C.Cl.[NH2:13][CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1>C(O)(C)C>[ClH:8].[Cl:8][CH2:7][CH2:6][CH2:5][CH:4]1[C:17]2[NH:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]=2[CH2:15][CH2:14][NH:13]1

Participants

4

Reactant 2

HCID 67652Tryptamine hydrochlorideHCID 2625984-Chlorobutyraldehyde Diethyl Acetal

Product 1

HCID 202449631-(3'-Chloropropyl)-1,2,3,4-tetrahydro-beta-carboline hydrochlorideYield 49.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

7 parts of γ-chlorobutyraldehyde diethyl acetal, 50 parts of isopropanol and 7.6 parts of 3-(β-aminoethyl)-indole hydrochloride were stirred for 7 hours at 83° C., and the mixture was cooled and then filtered under suction to give 5.5 parts (49.5%) of 1-(γ-chloropropyl)-1,2,3,4-tetrahydro-β-carboline hydrochloride of melting point 219°-221° C. The substance was identical to the product of Example 1.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationfiltered under suction

Sources & evidence

ORD record
ord-19f2150b2eba4e088eb5335875f2e280
Source dataset
uspto-grants-1986_01
Patent number
US04565870

Reaction notes

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