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

HRID 728701Notes

Reaction equation

HRID 728701 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 4 N aqueous sodium hydroxide solution to pH 13. After settling ha 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., the residual yellow oil (0.43 g) is dissolved in ethanol (2 cc) and then treated with a solution of fumaric acid (0.14 g) in ethanol (5 cc), concentrated to half the volume under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and treated with ethyl ether (20 cc). After 2 hours' stirring at a temperature in the region of 20° C., the solid formed is drained and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. N-Propyl-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide acid fumarate (0.38 g) is thereby obtained in the form of a pale yellow solid, m.p. 75-80° C. (melts forming a paste).

Workup

  1. customThe black reaction mixture
  2. filtrationfiltered
  3. stirringwith stirring with 4 N 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.
  8. dissolutionthe residual yellow oil (0.43 g) is dissolved in ethanol (2 cc)
  9. additiontreated with a solution of fumaric acid (0.14 g) in ethanol (5 cc)
  10. concentrationconcentrated to half the volume under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  11. additiontreated with ethyl ether (20 cc)
  12. stirringAfter 2 hours' stirring at a temperature in the region of 20° C.
  13. customthe solid formed
  14. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-bb4d5242b4ce42bda30a0e45f63ae52d
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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