Sulfuric Acid → 9-chloro-6-((E)-2-(4-fluorophenyl)prop-1-enyl)-1,2,3,4,5,6-hexahydro-3-methylazepino[4,5-b]indole

HRID 1045577Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)(O)[CH3:13])[C:6]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:5]=3[C:4]=2[CH:3]=1.OS(O)(=O)=O.[OH-].[K+]>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[C:12](/[C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)\[CH3:13])[C:6]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:5]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The title compound was prepared by following general procedure 6. 1-(9-Chloro-3-methyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-2-(4-fluorophenyl)propan-2-ol (100 mg, 0.259 mmol) was taken into 2.0 mL of 25% H2SO4 in water, and stirred at 90° C. for 3 h. The reaction was monitored by TLC and LCMS. The reaction mixture was cooled and basified with aq. KOH solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified using reverse phase chromatography to afford 12 mg of product as the TFA salt along with 9-chloro-6-(2-(4-fluorophenyl)allyl)-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole. Compound No. 82: 1H NMR (CDCl3, freebase) δ (ppm): 7.50-7.30 (m, 3H), 7.20-7.00 (m, 4H), 7.30-7.20 (d, 1H), 5.00-4.90 (t, 2H), 4.40-4.30 (d, 1H), 3.10-2.90 (m, 8H), 2.60 (s, 3H).

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe crude product was purified

Sources & evidence

ORD record: ord-1970d450cacc408f897b2172ef8b9beb
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569287B2

Reaction notes

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