6-Chloroindole → 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1003560Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.O.Cl.[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]3[CH2:17][CH2:18][NH:13][CH2:14][CH:15]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 871116-Chloroindole

HCID 2723901Piperonylamine

Product 1

HCID 100598546-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 61.2%

Procedure

Beginning with 4.0 gm (26.0 mMol) 6-chloro-1H-indole and 8.0 gm (52.0 mMol) 4-piperidone hydrochloride monohydrate, 3.7 gm (61%) of the title compound were recovered as a yellow solid.

Sources & evidence

ORD record: ord-347f641554d840e8beb39c827aa83cb1
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046215

Reaction notes

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