5-Cyclohexyltryptamine hydrochloride → (+/-) 6-cyclohexyl-1-(1-naphthalenylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride

HRID 1735819Notes

Reaction equation

HRID 1735819 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[CH:12]([CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[NH:13][CH2:14][CH2:15][C:6]2=1.Cl.[CH:28]1(C2C=C3C(NC=C3CCN)=CC=2)[CH2:33][CH2:32]C[CH2:30][CH2:29]1>Cl>[ClH:1].[CH:2]1([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7]2[CH:12]([CH2:16][C:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:20]=[CH:19][CH:18]=4)[NH:13][CH2:14][CH2:15][C:6]3=2)[CH2:32][CH2:33][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 187022465-Cyclohexyltryptamine hydrochlorideHCID 18933166(+/-) 6-methyl-1-(1-naphthalenylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride

Product 1

HCID 18933173(+/-) 6-cyclohexyl-1-(1-naphthalenylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochlorideYield 34.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of azalactone (prepared as described in Example 5) (1.09 g, 4.59 mmol) and 5-cyclohexyltryptamine hydrochloride (1.28 g, 4.59 mmol) in 1N HCl (70 mL) was heated to reflux for 14 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and the crude product isolated by filtration. The solid was recrystallized from ethanol (2×) to afford 690 mg of desired product as a pale solid hydrochloride salt.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 14 hours under nitrogen atmosphere
  3. customthe crude product isolated by filtration
  4. customThe solid was recrystallized from ethanol (2×)

Sources & evidence

ORD record
ord-d2753dc0db474dd2bb63d6ab5fb39926
Source dataset
uspto-grants-1996_07
Patent number
US05538981

Reaction notes

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