Triethylamine → 3-Chloro-N-[(R)-1-phenyl-2-[1-(4-pyridinyl)piperidin-4-yl-methoxy]ethyl]-1H-indole-6-carboxamide

HRID 32421Notes

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.C(N(CC)CC)C.Cl.Cl[C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1>CCO>[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]([C:39]4[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=4)[CH2:22][CH2:23]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a suspension of 3-chloro-N-[(R)-1-phenyl-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (1.0 g, 2.2 mmol) in 20 mL of EtOH was added triethylamine (1.56 mL, 11 mmol) and 4-chloropyridine hydrochloride (336 mg, 2.2 mmol). Heating the mixture at 120° C. in a sealed tube afforded, after purification (SiO2: 8:2:1 hexane:EtOAc:isopropylamine), 185 mg (16%) of the title compound.

Workup

customafforded
customafter purification (SiO2: 8:2:1 hexane:EtOAc:isopropylamine), 185 mg (16%) of the title compound

Sources & evidence

ORD record: ord-4c8b2e4d15ba461490dc21ab370042a8
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427632B2

Reaction notes

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