Piperonylamine → 6,7-dichloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1003567Notes

Reaction equation

[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.O.Cl.[NH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([C:6]([C:17]3[CH2:18][CH2:19][NH:14][CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 2723901Piperonylamine

HCID 122728026,7-dichloro-1H-indole

Product 1

HCID 185459816,7-dichloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 89.8%

Procedure

Beginning with 1.4 gm (7.5 mMol) 6,7-dichloro-1H-indole and 2.3 gm (15.0 mMol) 4-piperidone hydrochloride monohydrate, 1.8 gm (89%) of the title compound were recovered as a white solid.

Sources & evidence

ORD record: ord-9491ec2c6c5e4890a79722fceaef756a
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046215

Reaction notes

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