Hydrochloric Acid → N-(2,2-difluoroethyl)-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)benzamide hydrochloride

HRID 473924Notes

Reaction equation

[F:1][CH:2]([F:31])[CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[O:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:17]=3[CH:30]=2)=[CH:9][CH:8]=1)=[O:6].[ClH:32]>CO>[ClH:32].[F:31][CH:2]([F:1])[CH2:3][NH:4][C:5](=[O:6])[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[O:22][CH2:21][CH2:20][NH:19][CH2:18][C:17]=3[CH:30]=2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a slurry of 1,1-dimethylethyl 7-(4-{[(2,2-difluoroethyl)amino]carbonyl}phenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.95 g, 2.2 mmol) and methanol (30 mL) was added hydrogen chloride (4 M in dioxane, 3.3 mL, 13 mmol). The reaction mixture was heated (50° C.) for 1.5 hours then concentrated. The resulting residue was suspended in ethyl ether (15 mL) and the solid collected by filtration to give N-(2,2-difluoroethyl)-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)benzamide hydrochloride salt (0.65 g, 80% yield) as a white solid. MS (EI) for C18H18F2N2O2: 333 (MH+).

Workup

concentrationthen concentrated
filtrationthe solid collected by filtration

Sources & evidence

ORD record: ord-f6ef9c788add4ec48fcbc5b4e1ed20b1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637499B2

Reaction notes

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