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

HRID 343449

Reaction equation

HRID 343449 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. temperature(20 mL) was heated
  2. temperatureto reflux for 36 hours under nitrogen atmosphere

Sources & evidence

ORD record
ord-14035a2428ae4cf68ed227cef150498e
Source dataset
uspto-grants-1999_01
Patent number
US05861425

Linked notes

Loading…