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

HRID 1285201Notes

Reaction equation

HRID 1285201 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]=O.C(O)(C)C.[NH2:11][CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[ClH:1].[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:15]2[NH:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]=2[CH2:13][CH2:12][NH:11]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1150TryptamineHCID 3776IsopropanolHCID 2422004-Chlorobutanal

Product 1

HCID 202449631-(3'-Chloropropyl)-1,2,3,4-tetrahydro-beta-carboline hydrochlorideYield 31.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

200 parts of a 17.5% strength by weight solution of γ-chlorobutyraldehyde in xylene, 212 parts of isopropanol, 52 parts of 3-(β-aminoethyl)-indole and 388 parts of a 10% strength by weight aqueous sulfuric acid were stirred for 5 hours at 82° C., the mixture was cooled and the product was filtered off under suction and washed with 100 parts of isopropanol. 36 parts (31.6%) of 1-(γ-chloropropyl)-1,2,3,4-tetrahydro-β-carboline hydrochloride of melting point 216°-220° C. were obtained (cf. Example 1).

Workup

  1. temperaturethe mixture was cooled
  2. filtrationthe product was filtered off under suction
  3. washwashed with 100 parts of isopropanol

Sources & evidence

ORD record
ord-09ab39151d32450f94d927d48c533324
Source dataset
uspto-grants-1986_01
Patent number
US04565870

Reaction notes

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