Borane;tetrahydrofuran → HCID 9821192, compound

HRID 1383296Notes

Reaction equation

B.C1COCC1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][N:24]([C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=O)[CH2:23]2)[CH2:17][CH2:16]1>C1COCC1>[CH2:28]([N:24]1[CH2:25][CH2:26][CH2:27][CH:22]([CH2:21][N:18]2[CH2:17][CH2:16][N:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH3:7])[CH2:20][CH2:19]2)[CH2:23]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Borane-THF (1.0M, 5 mmol) was added dropwise to a THF solution (8 mL) of {3-[4-(2-methoxyphenyl)-piperazin-1-ylmethyl]-piperidin-1-yl}-phenyl-methanone (0.54 g, 1.37 mmol) from example 8 at 0° C. under nitrogen. The mixture was refluxed for 16 hours and after cooling to 0° C., the reaction was terminated by the addition of 2N-HCl (50 mL). After stirring for 1 hour, the solution was made basic with NaOH and the product extracted into ethyl acetate (3×35 mL). The combined organics were washed with water (50(mL), brine (50(mL) and dried over anhydrous sodium sulfate. Filtration and concentration in vacuum gave the required product (0.36 g, 69% yield). An ethanolic solution of the product was treated with a hot ethanolic solution of fumaric acid (2.0 equivalents) and afforded the fumarate salt of the titled compound as a light yellow colored solid.

Workup

temperatureThe mixture was refluxed for 16 hours
customthe reaction was terminated by the addition of 2N-HCl (50 mL)
extractionthe product extracted into ethyl acetate (3×35 mL)
washThe combined organics were washed with water (50(mL), brine (50(mL) and
dry with materialdried over anhydrous sodium sulfate
filtrationFiltration and concentration in vacuum

Sources & evidence

ORD record: ord-7d60aba2eff34a468fda6ddaa7bcd71d
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255302B1

Reaction notes

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