2-Methylpyrrolidine → HCID 14502158, compound

HRID 1165790Notes

Reaction equation

HRID 1165790 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.[CH3:25][CH:26]1[CH2:30][CH2:29][CH2:28][NH:27]1>C1(C)C=CC=CC=1>[CH3:25][CH:26]1[CH2:30][CH2:29][CH2:28][N:27]1[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]

Participants

4

Reactant 2

HCID 130032-MethylpyrrolidineHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

Product 1

HCID 14502158HCID 14502158, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of D series 2-(2-cyano-10-phenothiazinyl)-propyl methanesulphonate (6.8 g) in toluene (80 cc) and (2RS)-2-methylpyrrolidine (3.5 cc) is heated with stirring at 100° C. for 48 hours. After cooling to 25° C., the mixture is transferred into a separating funnel where it is washed with distilled water (2×200 cc) and brine (50 cc). The organic phase is dried over magnesium sulphate and filtered, and the filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) to give a residue which is purified by chromatography on a column (height: 35 cm; diameter: 3.2 cm) of silica (0.2-0.06 mm), eluting with a mixture of cyclohexane and ethyl acetate 70-30 (by volume) (1 liter), collecting fractions of 60 cc. Fractions 11 to 14 are pooled and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) to give 10-{1-[(2RS)-2-methyl-1-pyrrolidinyl]-2-propyl}-2-phenothiazinecarbonitrile, D series (0.5 g), in the form of a yellow oil.

Workup

  1. temperatureAfter cooling to 25° C.
  2. customthe mixture is transferred into a separating funnel
  3. washwhere it is washed with distilled water (2×200 cc) and brine (50 cc)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)
  7. customto give a residue which
  8. customis purified by chromatography on a column (height: 35 cm; diameter: 3.2 cm) of silica (0.2-0.06 mm)
  9. washeluting with a mixture of cyclohexane and ethyl acetate 70-30 (by volume) (1 liter)
  10. customcollecting fractions of 60 cc
  11. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-fa23672c55b6471ea9819d6f631567d1
Source dataset
uspto-grants-1990_03
Patent number
US04912105

Reaction notes

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