6-Nitro-1H-indole → 6-Nitro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].O.Cl.[NH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1>>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH:17]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 785026-Nitro-1H-indole

HCID 2723901Piperonylamine

Product 1

HCID 212682696-Nitro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Procedure

The title compound was prepared in a fashion similar to that described in Preparation 30 from 6-nitroindole (6.0 g, 37 mmol) and 4-piperidone hydrochloride hydrate (11.4 g, 74 mmol). The product was isolated as an orange solid. Yield 8.8 g (97%). mp 247-250° C.(dec.) FDMS m/e=243 (M+ of free base).

Workup

customThe product was isolated as an orange solid

Sources & evidence

ORD record: ord-2c9fbc8934b546a99ef05ddfa0376cbc
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172073B2

Reaction notes

Loading…