3-Methylpiperidine → HCID 15925282, compound

HRID 704188Notes

Reaction equation

HRID 704188 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[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]1>C1(C)C=CC=CC=1>[CH3:25][CH:26]1[CH2:31][CH2:30][CH2:29][N:28]([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])[CH2:27]1

Participants

4

Reactant 2

HCID 790813-MethylpiperidineHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

Product 1

HCID 15925282HCID 15925282, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (2RS)-2-(2-cyano-10-phenothiazinyl)-1-propyl methanesulphonate (14.4 g) and (3RS)-3-methylpiperidine (9.4 cc) in toluene (75 cc) is stirred under reflux for 20 hours. After cooling, the mixture is extracted with N aqueous hydrochloric acid solution (2×100 cc). The combined aqueous phases are alkalinized with caustic soda (d=1.33) to pH 13 and extracted with ethyl acetate (2×200 cc). The combined organic phases are washed successively with distilled water (2×50 cc) and with saturated aqueous sodium chloride solution (50 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 (14.4 g) is purified by chromatography on a column (height: 40 cm; diameter: 4 cm) of silica gel (0.2-0.063 mm), eluting with a mixture (80:20 by volume) (2.5 liters) of cyclohexane and ethyl acetate and collecting 100-cc fractions. The combined fractions 10 to 12 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-((2RS)-1-[(3RS)-3-Methyl-1-piperidyl]-2-propyl}-2-phenothiazinecarbonitrile (7.2 g) is thereby obtained in the form of a yellow oil, which is subsequently used as it is.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with N aqueous hydrochloric acid solution (2×100 cc)
  4. extractionextracted with ethyl acetate (2×200 cc)
  5. washThe combined organic phases are washed successively with distilled water (2×50 cc) and with saturated aqueous sodium chloride solution (50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  9. customThe residual yellow oil (14.4 g) is purified by chromatography on a column (height: 40 cm; diameter: 4 cm) of silica gel (0.2-0.063 mm)
  10. washeluting with a mixture (80:20 by volume) (2.5 liters) of cyclohexane and ethyl acetate
  11. customcollecting 100-cc fractions
  12. concentrationThe combined fractions 10 to 12 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-a9abb90568894d56bff5e9e473862630
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

Loading…