Sodium Bicarbonate → HCID 13923970, compound

HRID 2118486Notes

Reaction equation

HRID 2118486 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]2[C:10](=[O:14])[CH:11]=[CH:12][O:13][C:8]=2[CH:7]=1.Cl.Cl.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(=O)(O)[O-].[Na+]>CN(C)C=O.[I-].[Na+]>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:16]=[CH:15][C:9]3[C:10](=[O:14])[CH:11]=[CH:12][O:13][C:8]=3[CH:7]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 30186831-(2-Chlorophenyl)piperazine dihydrochlorideHCID 108475634H-1-Benzopyran-4-one, 7-(3-chloropropoxy)-

Product 1

HCID 13923970HCID 13923970, compound

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(3-chloropropoxy)-4H-benzopyran-4-one as prepared above in Preparation I (2.38 g; 10 mmol), 1-(2-chlorophenyl)piperazine dihydrochloride (2.96 g; 11 mmol), sodium bicarbonate (3 g; 35 mmol), sodium iodide (0.1 g; 0.6 mmole) in 50 ml dimethylformamide was mechanically stirred and heated at 85°-90° C. for seven hours. The solvent was then evaporated in vacuo and the residue partitioned between water and dichloromethane. The organic phase was treated with an excess of 10% HCl solution in methanol, evaporated in vacuo and the residue recrystallized from ethanol/ethyl acetate to yield 3.2 g of 7-[3-(4-(2-chlorophenyl)-1-piperazinyl)propoxy]-4H-1-benzopyran-4-one as its hydrochloride salt, mp 201°-203° C. (dec).

Workup

  1. temperatureheated at 85°-90° C. for seven hours
  2. customThe solvent was then evaporated in vacuo
  3. customthe residue partitioned between water and dichloromethane
  4. additionThe organic phase was treated with an excess of 10% HCl solution in methanol
  5. customevaporated in vacuo
  6. customthe residue recrystallized from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-072b1642352f4ae883db0927ae700dfd
Source dataset
uspto-grants-1987_07
Patent number
US04678787

Reaction notes

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