5-Methyltryptamine hydrochloride → (+/-) 6-methyl-1-(1-(2-methoxynaphthalenyl)methyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride

HRID 2294228Notes

Reaction equation

HRID 2294228 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:14]=[C:13]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[CH3:15][O:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]=1[CH2:27][CH:28]=O>C(O)C>[ClH:1].[CH3:2][C:3]1[CH:14]=[C:13]2[C:6](=[CH:5][CH:4]=1)[NH:7][C:8]1[CH:28]([CH2:27][C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:25]=[CH:26][C:17]=3[O:16][CH3:15])[NH:12][CH2:11][CH2:10][C:9]2=1

Participants

4

Reactant 2

HCID 69171455-Methyltryptamine hydrochlorideHCID 544795532-(2-Methoxynaphthalen-1-yl)acetaldehyde

Product 1

HCID 18933134(+/-) 6-methyl-1-(1-(2-methoxynaphthalenyl)methyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5-methyltryptamine hydrochloride (947 mg, 4.49 mmol.) in 20 mL of ethyl alcohol was added (2-methoxy-1-naphthyl)-acetaldehyde (1.0 g, 4.99 mmol.). The solution was heated to reflux under nitrogen atmosphere for 40 hours. The reaction mixture was cooled to ambient temperature and the crude product isolated by filtration. Recrystallization from ethyl alcohol/2-butanone afforded product as a pale solid (705 mg). (mp. 245.3° C.).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux under nitrogen atmosphere for 40 hours

Sources & evidence

ORD record
ord-5ad1ca591c424a489d2a830624c00e34
Source dataset
uspto-grants-1997_11
Patent number
US05688807

Reaction notes

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