Water → 4-Benzyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine

HRID 1524315Notes

Reaction equation

[H-].[Na+].[CH2:3]([N:10]([CH2:14][C:15]1[C:16](Cl)=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>C1COCC1>[CH2:3]([N:10]1[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[N:17][C:16]=2[O:13][CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Under a nitrogen atmosphere, to a suspension of sodium hydride (60% in oil, 1.99 g) in THF (30 ml) was added a solution of the compound (6.90 g) obtained in step 2 in THF (20 mL) at 0° C., and the mixture was stirred at 90° C. for 1 hr. The reaction mixture was cooled to 10° C., and poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 10→66% ethyl acetate/hexane) to give the title compound (4.51 g, 75%) as a pale-yellow oil.

Workup

temperatureThe reaction mixture was cooled to 10° C.
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous ammonium chloride solution and brine
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (solvent gradient; 10→66% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c2c95c416d1b4eee8d6c0d2c59660a2e
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079907B2

Reaction notes

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