Potassium Iodide → HCID 53787542, compound

HRID 1734089Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]1[S:13][C:12]2[CH2:11][CH2:10][CH2:9][C:8](=[O:14])[NH:7][C:6]=2[C:5]=1[CH2:15][CH3:16].Cl.[F:18][C:19]1[CH:33]=[CH:32][C:22]2[C:23]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[N:24][O:25][C:21]=2[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C1(C)C=CC=CC=1.O>[CH2:15]([C:5]1[C:6]2[NH:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][C:12]=2[S:13][C:4]=1[CH2:3][CH2:2][N:29]1[CH2:28][CH2:27][CH:26]([C:23]2[C:22]3[CH:32]=[CH:33][C:19]([F:18])=[CH:20][C:21]=3[O:25][N:24]=2)[CH2:31][CH2:30]1)[CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1.0 g of 2-(2-chloroethyl)-3-ethyl-4,6,7,8-tetrahydro- 5H-thieno[3,2-b]azepin-5-one, 1.0 g of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine hydrochloride, 4.0 g of potassium carbonate and 1.5 g of potassium iodide in 25 ml of dimethylformamide and 25 ml of toluene was stirred at 100° C. for 3 hours and poured into water. The toluene layer was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on a silica gel and recrystallized from isopropyl alcohol to give 0.45 g of 3-ethyl-2-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-one 3/4 hydrate, m.p. 115°-117° C.

Workup

washThe toluene layer was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography on a silica gel
customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record: ord-9e600e796a754d308dfc5e6ce97be8a6
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05532240

Reaction notes

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