2-(7-bromo-1H-indol-3-yl)ethan-1-amine hydrochloride → (+/-) 8-bromo-1-(1-naphthalenylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride

HRID 1735802Notes

Reaction equation

HRID 1735802 reaction equation
[ClH:1].C[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.[Br:28]C1C=CC=C2C=1NC=C2CCN>Cl>[ClH:1].[Br:28][C:10]1[CH:11]=[CH:3][CH:4]=[C:5]2[C:9]=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

Participants

4

Reactant 2

HCID 187022612-(7-bromo-1H-indol-3-yl)ethan-1-amine hydrochlorideHCID 18933166(+/-) 6-methyl-1-(1-naphthalenylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride

Product 1

HCID 18933157(+/-) 8-bromo-1-(1-naphthalenylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochlorideYield 11.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of azalactone (prepared as described in Example 5) (55 g, 6.53 mmol) and 7-bromotryptamine hydrochloride (1.50 g, 5.44 mmol) in 1N HCl (100 mL) was heated to reflux for 24 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and the crude product isolated by filtration. The brown solid was triturated with isopropyl alcohol (3×50 mL) and washed with diethyl ether (3×50 mL). Recrystallization from ethanol afforded 260 mg of desired product as the hydrochloride salt. (mp=231°-233° C., dec.)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours under nitrogen atmosphere
  3. customthe crude product isolated by filtration
  4. customThe brown solid was triturated with isopropyl alcohol (3×50 mL)
  5. washwashed with diethyl ether (3×50 mL)
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-e2515ef74c824714b191f262363c4504
Source dataset
uspto-grants-1996_07
Patent number
US05538980

Reaction notes

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