2-Cyclohexylacetaldehyde → 6-methyl-1-(cyclohexylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride

HRID 1597905Notes

Reaction equation

HRID 1597905 reaction equation
[CH:1]1([CH2:7][CH:8]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:10].[CH3:11][C:12]1[CH:23]=[C:22]2[C:15]([NH:16][CH:17]=[C:18]2[CH2:19][CH2:20][NH2:21])=[CH:14][CH:13]=1>C(O)C>[ClH:10].[CH3:11][C:12]1[CH:23]=[C:22]2[C:15](=[CH:14][CH:13]=1)[NH:16][C:17]1[CH:8]([CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[NH:21][CH2:20][CH2:19][C:18]2=1

Participants

4

Reactant 2

HCID 3166272-CyclohexylacetaldehydeHCID 69171455-Methyltryptamine hydrochloride

Product 1

HCID 187022656-methyl-1-(cyclohexylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of cyclohexylacetaldehyde (631 mg, 5.0 mmol.) and 5-methyltryptamine hydrochloride (1.0 g, 4.3 mmol.) in ethanol (20 mL) was heated to reflux for 36 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and the crude product isolated by filtration. The solid was triturated with ethanol and washed with diethyl ether. The product was isolated by filtration (731 mg). m/e=282, mp 230° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 36 hours under nitrogen atmosphere

Sources & evidence

ORD record
ord-5a1d8961a3f04c7ea69fa044208ab0c4
Source dataset
uspto-grants-1998_04
Patent number
US05736544

Reaction notes

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