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

HRID 1692588Notes

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-ef1dd7802d3141059e8638f6d70ff7aa
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158617B2

Reaction notes

Loading…