Potassium Carbonate → 4-{4-[4-(4-Fluorobenzamido)piperidinomethyl]phenylmethoxyl}-2-isopropylidenecoumaran-3-one

HRID 381683Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[C:13](=[O:23])[C:14](=[C:20]([CH3:22])[CH3:21])[O:15]3)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:30][C:31]1[CH:45]=[CH:44][C:34]([C:35]([NH:37][CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[O:36])=[CH:33][CH:32]=1>CN(C)C=O>[F:30][C:31]1[CH:45]=[CH:44][C:34]([C:35]([NH:37][CH:38]2[CH2:43][CH2:42][N:41]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]4[CH:19]=[CH:18][CH:17]=[C:16]5[C:12]=4[C:13](=[O:23])[C:14](=[C:20]([CH3:22])[CH3:21])[O:15]5)=[CH:5][CH:4]=3)[CH2:40][CH2:39]2)=[O:36])=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 570 mg 4-(4-chloromethyl-phenylmethoxy)-2-isopropylidenecoumaran-3-one (preparation 2), 240 mg potassium carbonate, 400 mg 4-(4-fluorobenzamido)piperidine and 15 ml dimethylformamide is warmed to 60° C. for 3 hours, then evaporated, mixed with water and extracted with ethyl acetate. After evaporation of the extract, the residue (0.6 g) is purified by silica gel chromatography (eluent ethyl acetate) to give 180 mg (19%) of the desired compound, m.p. 205-208° C.

Workup

customevaporated
additionmixed with water
extractionextracted with ethyl acetate
customAfter evaporation of the extract
customthe residue (0.6 g) is purified by silica gel chromatography (eluent ethyl acetate)

Sources & evidence

ORD record: ord-aaaeabbf1dca43189727a5018d80d803
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06307051B1

Reaction notes

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