Tetrahydrofuran → HCID 23142306, compound

HRID 2218856

Reaction equation

CC1(C)[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:4][CH2:3]1.[CH2:21](N(CC)CC)C.[C:28](Cl)(=[O:32])[CH2:29][CH2:30][CH3:31].C(=O)([O-])O.[Na+].O1[CH2:43][CH2:42][CH2:41][CH2:40]1>C(OCC)(=O)C>[CH2:41]([C:42]1([CH2:43][CH3:21])[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]2[CH2:15][CH2:16][N:17]([C:28](=[O:32])[CH2:29][CH2:30][CH3:31])[CH2:18][CH2:19]2)[CH2:4][CH2:3]1)[CH3:40]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-[2-(4,4-dimethylcyclohexyl)phenyl]piperazine (30 mg, 0.10 mmol) produced in Example (83a) in tetrahydrofuran (1 mL) was added triethylamine (15 mg, 0.15 mmol), followed by stirring at an external temperature of 0° C. Butyryl chloride (0.015 mL, 0.14 mmol) was added to the reaction mixture while stirring, and the stirring was continued for 9 hours and 30 minutes at an external temperature of 0° C. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and filtered through Celite, and the filtrate was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 27 mg of the title compound as a yellow solid.

Workup

stirringwhile stirring
washThe organic layer was washed with water
filtrationfiltered through Celite
concentrationthe filtrate was concentrated
customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record: ord-5fb9d8f480d444178b075c450a11506a
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410971B2

Linked notes

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