Acetone → 3-Chloro-N-[(R)-1-phenyl-2-(1-isopropylpiperidin-4-yl-methoxy)ethyl]-1H-indole-6-carboxamide hydrochloride

HRID 32417Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][C@H:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[CH3:30][C:31]([CH3:33])=O>>[ClH:1].[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][C@H:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:15][O:16][CH2:17][CH:18]3[CH2:19][CH2:20][N:21]([CH:31]([CH3:33])[CH3:30])[CH2:22][CH2:23]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

Reactant 2

HCID 180Acetone

HCID 9866338HCID 9866338, compound

Product 1

HCID 693108103-Chloro-N-[(R)-1-phenyl-2-(1-isopropylpiperidin-4-yl-methoxy)ethyl]-1H-indole-6-carboxamide hydrochloride

Procedure

Using alkylation method A, 3-chloro-N-[(R)-1-phenyl-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (200 mg, 0.45 mmol) and acetone (0.33 mL, 4.5 mmol) afforded, after purification (SiO2: 8:2:1 hexane:EtOAc:isopropylamine) and conversion to the HCl salt by general method B, 120 mg (55%) of the title compound.

Workup

customafforded
customafter purification (SiO2: 8:2:1 hexane:EtOAc:isopropylamine) and conversion to the HCl salt by general method B, 120 mg (55%) of the title compound

Sources & evidence

ORD record: ord-8732b08ab144473298fa65faa65bf153
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427632B2

Reaction notes

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