4-Vinylpyridine → HCID 59368262, compound

HRID 1481402Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:5]=3[C:4]=2[CH:3]=1.[CH:17]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)=[CH2:18].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:18][CH2:17][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:5]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

The title compound was prepared by following general procedure 4. 9-Chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (100 mg, 0.42 mmol), tetra n-butyl ammonium chloride (6 mg, 0.025 mmol), 4-vinylpyridine (53 mg, 0.51 mmol) were taken into 50% NaOH (3 mL). The reaction mixture was heated overnight at 110° C. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was extracted with ethyl acetate and water, the organic layer was dried over Na2SO4, and concentrated under reduced pressure to obtain 40 mg of 9-chloro-3-methyl-6-(2-(pyridin-4-yl)ethyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole as the TFA salt after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min., injection vol. 5 mL).

Workup

customThe title compound was prepared
customAfter completion of reaction
extractionthe reaction mixture was extracted with ethyl acetate and water
dry with materialthe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-77cc3937537c4d5598c5999e732a88f0
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409910B2

Reaction notes

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