4-Morpholinecarbonyl chloride → (6-Fluoro-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-morpholin-4-yl-methanone

HRID 856989Notes

Reaction equation

Br[C:2]1[C:22]([F:23])=[CH:21][C:5]2[O:6][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.C([Li])CCC.[N:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(=O)(O)[O-].[Na+]>C(OCC)C>[F:23][C:22]1[C:2]([C:35]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:36])=[CH:3][C:4]2[O:8][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:6][C:5]=2[CH:21]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a cooled (−78° C.) solution of 5-bromo-6-fluoro-2,2-diphenyl-benzo[1,3]dioxole (17.59 g, 47.4 mmol) in diethyl ether (300 ml) was slowly added a solution of n-butyl lithium in hexanes (1.6M, 30 ml, 48 mmol, 1.0 eq.). The reaction mixture was stirred 1 h at −78° C. before the addition of 4-morpholinecarbonylchloride (8.5 g, 56.9 mmol, 1.2 eq.). The reaction mixture was allowed to warm to 20° C. and poured into an aqueous solution of sodium bicarbonate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine. Volatiles were removed in vacuo. Purification by flash chromatography afforded (6-fluoro-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-morpholin-4-yl-methanone compound (13.0 g, 68%) as a light yellow solid.

Workup

extractionThe aqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with brine
customVolatiles were removed in vacuo
customPurification by flash chromatography

Sources & evidence

ORD record: ord-dc303e1cc50343c3afbc0eee43a6ca36
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144890B2

Reaction notes

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