Methane → Mafoprazine

HRID 1648781Notes

Reaction equation

HRID 1648781 reaction equation
[OH-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([O:14][CH3:15])[CH:8]=1)(=[O:5])[CH3:4].Cl[CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[CH2:22][CH2:21]1.C>CS(C)=O.C(O)(C)C>[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[CH2:22][CH2:21]2)=[C:9]([O:14][CH3:15])[CH:8]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 297MethaneHCID 14798Sodium HydroxideHCID 30805943-MethoxyacetaminophenHCID 20481759HCID 20481759, compound

Product 1

HCID 71241MafoprazineYield 74%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

1.13 g of powdery sodium hydroxide are added under nitrogen atmosphere to a solution of 5.08 g of 4-acetamido-2-methoxyphenol in 70 ml of anhydrous dimethylsulfoxide. The mixture is stirred at 50° C. for 2 hours. A solution of 6 g of 1-(3-chloro-n-propyl)-4-(2-fluorophenyl)-piperazine in 20 ml of anhydrous dimethylsulfoxide is added dropwise at 20° C. to the mixture, and said mixture is stirred at 100° C. for 1.5 hours. After cooling, the reaction mixture is poured into ice-water. The crystalline precipitates are collected by filtration, whereby a crude product is obtained. The mother liquor obtained after isolating the crude product is extracted with chloroform. The extract is washed with water, dried and then evaporated under reduced pressure to remove the solvent, whereby another crude product is obtained. Both crude products obtained above are dissolved in hot isopropyl alcohol and then treated with activated charcoal. 6.95 of 1-[3-(4-acetamido-2-methoxyphenoxy)-n-propyl]-4-(2-fluorophenyl)-piperazine are thereby obtained as colorless needles. Yield: 74%

Workup

  1. stirringis stirred at 100° C. for 1.5 hours
  2. temperatureAfter cooling
  3. customThe crystalline precipitates
  4. filtrationare collected by filtration, whereby a crude product
  5. customis obtained
  6. customThe mother liquor obtained
  7. customafter isolating the crude product
  8. extractionis extracted with chloroform
  9. washThe extract is washed with water
  10. customdried
  11. customevaporated under reduced pressure
  12. customto remove the solvent, whereby another crude product
  13. customis obtained
  14. customBoth crude products obtained

Sources & evidence

ORD record
ord-beb4e2ddb1764abcb6bd1de9162261b4
Source dataset
uspto-grants-1983_11
Patent number
US04413006

Reaction notes

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