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

HRID 2294227Notes

Reaction equation

HRID 2294227 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-3279229cbce64f429807c045bd93e80e
Source dataset
uspto-grants-1997_11
Patent number
US05688807

Reaction notes

Loading…