Pyrrolidine → HCID 14502142, compound

HRID 1165785Notes

Reaction equation

HRID 1165785 reaction equation
CS(O[CH2:6][CH:7]([N:9]1[C:22]2[CH:21]=[C:20]([C:23]#[N:24])[CH:19]=[CH:18][C:17]=2[S:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:8])(=O)=O.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[N:25]1([CH2:6][CH:7]([N:9]2[C:22]3[CH:21]=[C:20]([C:23]#[N:24])[CH:19]=[CH:18][C:17]=3[S:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH3:8])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

Product 1

HCID 14502142HCID 14502142, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(2-cyano-10-phenothiazinyl)-(2RS)-1-propyl methanesulphonate (10 g) and pyrrolidine (11.6 cc) in toluene (50 cc) is brought to 90° C. while stirring for 24 hours. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and the residue is taken up in ethyl ether (200 cc) and a 4N aqueous solution of sodium hydroxide (15 cc). After stirring for 10 minutes, the organic phase is decanted and washed with a saturated aqueous solution of sodium chloride (3×25 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 20° C. The residual oil (11.3 g) is dissolved in a 0.05N aqueous solution of hydrochloric acid (60 cc). This solution is washed with ethyl ether (100 cc), then rendered alkaline with an excess of a N aqueous solution of sodium hydroxide and extracted with ethyl ether (100 cc). The organic phase is washed with a saturated aqueous solution of sodium chloride (50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 20° C. The residual yellow oil (9.5 g) is purified on a column (height: 30 cm; diameter: 5.8 cm) of silica gel (0.04-0.063 mm) under a slight overpressure of nitrogen (40 kPa), eluting with a liter of a mixture of methylene chloride and methanol (95-5 by volume) and collecting fractions of 100 cc. Fractions 3 to 10 are pooled and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonitrile (5.45 g) is thus obtained in the form of a yellow oil.

Workup

  1. customis brought to 90° C.
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  4. stirringAfter stirring for 10 minutes
  5. customthe organic phase is decanted
  6. washwashed with a saturated aqueous solution of sodium chloride (3×25 cc)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 20° C
  10. dissolutionThe residual oil (11.3 g) is dissolved in a 0.05N aqueous solution of hydrochloric acid (60 cc)
  11. washThis solution is washed with ethyl ether (100 cc)
  12. extractionextracted with ethyl ether (100 cc)
  13. washThe organic phase is washed with a saturated aqueous solution of sodium chloride (50 cc)
  14. dry with materialdried over magnesium sulphate
  15. filtrationfiltered
  16. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 20° C
  17. customThe residual yellow oil (9.5 g) is purified on a column (height: 30 cm; diameter: 5.8 cm) of silica gel (0.04-0.063 mm) under a slight overpressure of nitrogen (40 kPa)
  18. washeluting with a liter of a mixture of methylene chloride and methanol (95-5 by volume)
  19. customcollecting fractions of 100 cc
  20. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-29d8cf6c915c4481a7c59439123f7647
Source dataset
uspto-grants-1990_03
Patent number
US04912105

Reaction notes

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