Sodium Hydroxide → HCID 59368251, compound

HRID 1045562Notes

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.[OH-].[Na+].[Cl:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:26]=[CH2:27])[CH:25]=1>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:27][CH2:26][C:24]3[CH:23]=[N:22][CH:21]=[C:20]([Cl:19])[CH:25]=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: 60 °C

Procedure

The title compound was prepared by following general procedure 4. To a solution of 9-chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (100 mg, 0.42 mmol) in 50% aq. NaOH solution (5 mL) tetra n-butyl ammonium chloride (9 mg, 0.03 mmol) followed by 3-chloro-5-vinylpyridine (65 mg, 0.47 mmol) was added. The reaction mixture was heated at 60° C. for 8 h. After completion of reaction, the reaction mixture was diluted with water, extracted with ethyl acetate; the organic layer was dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by reverse phase chromatography to afford 5 mg of 9-chloro-6-(2-(5-chloropyridin-3-yl)ethyl)-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole as the TFA salt.

Workup

customThe title compound was prepared
additionwas added
customAfter completion of reaction
extractionextracted with ethyl acetate
dry with materialthe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe crude product was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-31bd2b701c324f759f5751f530ec0d27
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569287B2

Reaction notes

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