Hydrochloric Acid → N-(3-Methylbutyl)-10-[(2RS)-1-(N-ethyl-N-methylamino)-2-propyl]-2-phenothiazinecarboxamide hydrochloride

HRID 728723Notes

Reaction equation

HRID 728723 reaction equation
[CH3:1][CH:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH:22]([CH3:28])[CH2:23][N:24]([CH2:26][CH3:27])[CH3:25])[C:10]=2[CH:9]=1)=S.[ClH:30].C(O)(=O)/C=C/C(O)=[O:35]>C(O)C.C(OC(C)C)(C)C>[ClH:30].[CH3:1][CH:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH:22]([CH3:28])[CH2:23][N:24]([CH2:26][CH3:27])[CH3:25])[C:10]=2[CH:9]=1)=[O:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 444972Fumaric AcidHCID 14536598N-(3-Methylbutyl)-10-[(2RS)-1-(N-ethyl-N-methylamino)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 14536601N-(3-Methylbutyl)-10-[(2RS)-1-(N-ethyl-N-methylamino)-2-propyl]-2-phenothiazinecarboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

N-(3-Methylbutyl)-10-[(2RS)-1-(N-ethyl-N-methyl-amino)-2-propyl]-2-phenothiazinecarbothioamide (0.3 g) is dissolved in a solution of fumaric acid (81 mg) in absolute ethanol (5 cc) and the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange product of meringue-like consistency is dissolved in acetic acid (5 cc) and mercuric acetate (0.23 g) is added. The orange suspension obtained is stirred for 16 hours at a temperature in the region of 20° C. The reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 60° C. The residue is taken up with distilled water (10 cc) and filtered and the filtrate is alkalinized with caustic soda (d=1.33) to pH 13 and extracted with ethyl acetate (2×10 cc). The combined organic phases are washed with saturated aqueous sodium chloride solution (10 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow oil (0.15 g) is dissolved in ethyl acetate (2 cc), and isopropyl ether (20 cc) is added. The solution obtained is cooled to a temperature in the region of 5° C. and a solution (5.1 cc) of 0.065N hydrochloric acid in isopropyl ether is added dropwise and with stirring. The precipitate formed is drained, washed with isopropyl ether (3×5 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. N-(3-Methylbutyl)-10-[(2RS)-1-(N-ethyl-N-methylamino)-2-propyl]-2-phenothiazinecarboxamide hydrochloride (0.13 g) is thereby obtained in the form of an off-white solid, m.p. 110-120° C. (melts forming a paste).

Workup

  1. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  2. dissolutionThe residual orange product of meringue-like consistency is dissolved in acetic acid (5 cc)
  3. additionmercuric acetate (0.23 g) is added
  4. customThe orange suspension obtained
  5. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 60° C
  6. filtrationfiltered
  7. extractionextracted with ethyl acetate (2×10 cc)
  8. washThe combined organic phases are washed with saturated aqueous sodium chloride solution (10 cc)
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  12. dissolutionThe residual yellow oil (0.15 g) is dissolved in ethyl acetate (2 cc)
  13. additionisopropyl ether (20 cc) is added
  14. customThe solution obtained
  15. temperatureis cooled to a temperature in the region of 5° C.
  16. stirringwith stirring
  17. customThe precipitate formed
  18. washwashed with isopropyl ether (3×5 cc)
  19. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-75c505e5d8c74878b7fc9877017f92ad
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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