Potassium Iodide → HCID 13207817, compound

HRID 1649136Notes

Reaction equation

[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:15][CH2:16][CH2:17][C:18]1[C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[O:20][N:19]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[F:27][C:25]1[CH:24]=[CH:23][C:22]2[C:18]([CH2:17][CH2:16][CH2:15][N:5]3[CH2:6][CH2:7][C:2]([OH:1])([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:3][CH2:4]3)=[N:19][O:20][C:21]=2[CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 50 ml of dry dimethylformamide was added, 6.0 g of 4-hydroxy-4-phenylpiperidine, 8.0 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 13.0 g of sodium bicarbonate, and a few crystals of potassium iodide. After stirring at 80° C. for one hr, the mixture was cooled, filtered, and the filtrate evaporated to an oil. The oil was stirred with 100 ml water for five mins, and then extracted with ether/ethyl acetate. The organic layer was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvents were evaporated. Trituration with ether gave 3.0 g (25%) of product, mp 133°-137° C. Recrystallization twice from ethyl ether gave the analytical sample, mp 138°-139° C.

Workup

temperaturethe mixture was cooled
filtrationfiltered
customthe filtrate evaporated to an oil
stirringThe oil was stirred with 100 ml water for five mins
extractionextracted with ether/ethyl acetate
washThe organic layer was washed with water (2×), saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtering
customthe solvents were evaporated

Sources & evidence

ORD record: ord-2bccf4bc0e114ae3b1b4c70d90afb61f
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04415581

Reaction notes

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