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

HRID 725052Notes

Reaction equation

HRID 725052 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-d59cff0b4bdd464fa6cd03d48fa9c516
Source dataset
uspto-grants-1998_01
Patent number
US05705519

Reaction notes

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