Acetic Acid → N-propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

HRID 1109533Notes

Reaction equation

HRID 1109533 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:21]([CH3:28])[CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:9]=2[CH:8]=1)=S)[CH2:2][CH3:3].C(O)(=[O:31])C>O.C(OCC)(=O)C>[CH2:1]([NH:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:21]([CH3:28])[CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:9]=2[CH:8]=1)=[O:31])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 14536531HCID 14536531, compound

Product 1

HCID 9800851N-propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mercuric acetate (0.38 g) is added with stirring to a solution of N-propyl-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide neutral fumarate (0.6 g) in acetic acid (10 cc), and stirring is continued for 4 hours 30 minutes at a temperature in the region of 20° C. The black reaction mixture is diluted with distilled water (25 cc) and ethyl acetate (50 cc) and then filtered and alkalinized with stirring with 4N aqueous sodium hydroxide solution to pH 13. After settling has taken place, the organic phase is separated and the aqueous phase is extracted with ethyl acetate (20 cc). The combined organic phases are washed successively with saturated aqueous sodium chloride solution (50 cc). After drying over magnesium sulphate, filtration and concentration to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C., N-propyl-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide (0.43 g) is obtained in the form of a yellow oil.

Workup

  1. customThe black reaction mixture
  2. filtrationfiltered
  3. stirringwith stirring with 4N aqueous sodium hydroxide solution to pH 13
  4. customthe organic phase is separated
  5. extractionthe aqueous phase is extracted with ethyl acetate (20 cc)
  6. washThe combined organic phases are washed successively with saturated aqueous sodium chloride solution (50 cc)
  7. dry with materialAfter drying over magnesium sulphate, filtration and concentration to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-348a9474552d443fa785dfbba254f2ca
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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