Sodium Hydroxide → HCID 70594441, compound

HRID 904066Notes

Reaction equation

HRID 904066 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=3)[C:12]([CH3:25])([CH3:24])[N:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>O>[ClH:1].[ClH:1].[CH3:22][N:21]([CH3:23])[C:18]1[CH:17]=[CH:16][C:15]([C@H:13]2[CH2:14][C@@H:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=3)[NH:11][C:12]2([CH3:24])[CH3:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23333475HCID 23333475, compound

Product 1

HCID 70594441HCID 70594441, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7 g. of 2-(p-methoxyphenyl)-5,5-dimethyl-4-(p-dimethylaminophenyl)-1-pyrroline hydrochloride in water is made alkaline with 3-N sodium hydroxide and extracted with methylene chloride. The organic phase is washed with water and dried over sodium sulfate. The oil which remains after removal of the solvent is taken up in 150 ml. of absolute ethanol and the solution treated with 5 g. of sodium borohydride. The mixture is then stirred at room temperature for 12 hours under nitrogen. Subsequently, the mixture is evaporated to dryness under reduced pressure and the residue suspended in water by intensive stirring. The non-dissolved constituent is filtered off, dried and recrystallized from n-pentane. The thus-purified base is taken up in ethanolic hydrochloric acid, again evaporated to dryness under reduced pressure and the residue recrystallized from ethanol/acetone. There is obtained cis-3-(p-dimethylaminophenyl)-2,2-dimethyl-5-(p-methoxyphenyl)-pyrrolidine dihydrochloride, having a melting point of 180° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customafter removal of the solvent
  5. additionof absolute ethanol and the solution treated with 5 g
  6. customSubsequently, the mixture is evaporated to dryness under reduced pressure
  7. filtrationThe non-dissolved constituent is filtered off
  8. customdried
  9. customrecrystallized from n-pentane
  10. customagain evaporated to dryness under reduced pressure
  11. customthe residue recrystallized from ethanol/acetone

Sources & evidence

ORD record
ord-0e92644e8c3e4fbaaacdeead602b7722
Source dataset
uspto-grants-1980_10
Patent number
US04230623

Reaction notes

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