Hydrochloric Acid → 4-(2-fluoro-benzenesulfonyl)-2,2-dimethyl-8-piperazin-1-yl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1270103Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[O:22][C:21]([CH3:25])([CH3:24])[CH2:20][N:19]([S:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[F:35])(=[O:28])=[O:27])[C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(O)C>[F:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[S:26]([N:19]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:23]=2[O:22][C:21]([CH3:25])([CH3:24])[CH2:20]1)(=[O:28])=[O:27]

Participants

Conditions

Temperature: 100 °C

Procedure

4-[4-(2-Fluoro-benzenesulfonyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl]-piperazine-1-carboxylic acid tert-butyl ester (470 mg, 0.93 mmol) was dissolved in 3 ml ethanol. To this solution was added 1 ml of 10% ethanolic hydrochloric acid solution. The mixture was heated at 100° C. (steam bath) for 15 minutes, and then cooled to room temperature at which time a white crystalline solid formed. The solid was collected by filtration and dried at 70° C. under vacuum to provide 160 mg of 4-(2-fluoro-benzenesulfonyl)-2,2-dimethyl-8-piperazin-1-yl-3,4-dihydro-2H-benzo[1,4]oxazine as a hydrochloride salt. MP: 222.9–227.1° C. MS: (M+H) 479.

Workup

temperaturecooled to room temperature at which time a white crystalline solid
customformed
filtrationThe solid was collected by filtration
customdried at 70° C. under vacuum

Sources & evidence

ORD record: ord-0173768f629d422193d357174da388b2
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202241B2

Reaction notes

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