Potassium Iodide → 2-(2-(4-(6-fluorobenzo(b)furan-3-yl)piperidin-1-yl)ethyl)-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-one

HRID 2294870Notes

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[CH:5]=1.Cl.[F:16][C:17]1[CH:18]=[CH:19][C:20]2[C:24]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:23][O:22][C:21]=2[CH:31]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C1(C)C=CC=CC=1.CN(C)C=O>[F:16][C:17]1[CH:18]=[CH:19][C:20]2[C:24]([CH:25]3[CH2:26][CH2:27][N:28]([CH2:2][CH2:3][C:4]4[S:13][C:12]5[CH2:11][CH2:10][CH2:9][C:8](=[O:14])[NH:7][C:6]=5[CH:5]=4)[CH2:29][CH2:30]3)=[CH:23][O:22][C:21]=2[CH:31]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2.0 g of 2-(2-chloroethyl)-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-one, 2.2 g of 4-(6-fluorobenzo(b)furan-3-yl)piperidine hydrochloride, 2.6 g of potassium carbonate, 1.44 g of potassium iodide, 20 ml of dimethylformamide and 20 ml of toluene was stirred at 80° C. for 8 hours and then poured into water. The toluene layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate to give 2-(2-(4-(6-fluorobenzo(b)furan-3-yl)piperidin-1-yl)ethyl)-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-one, m.p. 176°-178° C.

Workup

washThe toluene layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-031317aa69f443419835c0b0c224b7b6
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05691330

Reaction notes

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