Cyclohexene → HCID 49832111, compound

HRID 880826Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([O:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O.C1CCCCC=1>O1CCOCC1.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([O:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)=[C:9]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 575 mg (1.41 mmol) of 7-nitro-3-phenyl-4-(3-piperidin-1-yl-propoxy)-2H-isoquinolin-1-one (cmpd. 35) in dioxane (15 mL), cyclohexene (5 mL, 49.4 mmol) and 250 mg of palladium on carbon (10 wt. % loading) were added and the mixture was heated at 100° C. under argon atmosphere for 3 hours. The mixture was cooled to room temperature and filtered through a celite pad, which was then washed with dioxane. The solvent was concentrated under reduced pressure and the resulting crude was purified by flash chromatography (eluant: dichloromethane/methanol/acetone/7N ammonia in methanol: 90/5/5/1) to afford 210 mg of the title compound (39%).

Workup

additionwere added
temperatureThe mixture was cooled to room temperature
filtrationfiltered through a celite pad, which
washwas then washed with dioxane
concentrationThe solvent was concentrated under reduced pressure
customthe resulting crude was purified by flash chromatography (eluant: dichloromethane/methanol/acetone/7N ammonia in methanol: 90/5/5/1)

Sources & evidence

ORD record: ord-0b7714bff1c747dfa092ca30d1fe8aae
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993594B2

Reaction notes

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