Sodium Bicarbonate → HCID 85071360, compound

HRID 381684Notes

Reaction equation

HRID 381684 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][O:10][C:11]2[CH:19]=[C:18]3[C:14]([C:15](=[O:29])[C:16](=[CH:20][CH:21]=[CH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:17]3)=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])O.[Na+].[F:35][C:36]1[CH:50]=[CH:49][C:39]([C:40]([NH:42][CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[O:41])=[CH:38][CH:37]=1>CN(C)C=O>[F:35][C:36]1[CH:50]=[CH:49][C:39]([C:40]([NH:42][CH:43]2[CH2:48][CH2:47][N:46]([CH2:2][C:3]3[CH:4]=[C:5]([CH2:9][O:10][C:11]4[CH:19]=[C:18]5[C:14]([C:15](=[O:29])[C:16](=[CH:20][CH:21]=[CH:22][C:23]6[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=6)[O:17]5)=[CH:13][CH:12]=4)[CH:6]=[CH:7][CH:8]=3)[CH2:45][CH2:44]2)=[O:41])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 47782264-fluoro-N-(piperidin-4-yl)benzamideHCID 57299650HCID 57299650, compound

Product 1

HCID 85071360HCID 85071360, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 520 mg 6-(3-chloromethyl-phenylmethoxy)-2-cinnamylidenecoumaran-3-one (preparation 6), 150 mg sodium hydrogencarbonate, 330 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 is purified by silica gel chromatography (eluent ethyl acetate) to give 500 mg (65%) of the desired compound, m.p. 126-128° C.

Workup

  1. customevaporated
  2. additionmixed with water
  3. extractionextracted with ethyl acetate
  4. customAfter evaporation of the extract
  5. customthe residue is purified by silica gel chromatography (eluent ethyl acetate)

Sources & evidence

ORD record
ord-1e629a4246094ccd8e2d92642873b090
Source dataset
uspto-grants-2001_10
Patent number
US06307051B1

Reaction notes

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