Piperidine → HCID 14536614, compound

HRID 1109538Notes

Reaction equation

HRID 1109538 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CS(O[CH2:12][CH:13]([N:15]1[C:28]2[CH:27]=[C:26]([C:29]#[N:30])[CH:25]=[CH:24][C:23]=2[S:22][C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:14])(=O)=O>C1(C)C(C)=CC=CC=1>[N:1]1([CH2:14][CH:13]([N:15]2[C:28]3[CH:27]=[C:26]([C:29]#[N:30])[CH:25]=[CH:24][C:23]=3[S:22][C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

Product 1

HCID 14536614HCID 14536614, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Piperidine (19.8 cc) is added to a suspension of 2-(2-cyano-10-phenothiazinyl)-1-propyl methane-sulphonate (36.05 g) in xylene (360 cc). The mixture is brought to reflux for 19 hours. After cooling, the mixture is washed with distilled water (6×150 cc). The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness at 50° C. under reduced pressure (30 mm Hg; 4 kPa). The residue is purified by chromatography on a column (height: 96 cm; diameter: 4.8 cm) of silica gel (0.06-0.2 mm), eluting with 90:10, 85:15, 80:20 and 75:25 (by volume) mixtures (4 liters, 4 liters and 4 liters, respectively) of cyclohexane and ethyl acetate and collecting 500- cc fractions. The first 9 liters are discarded and fractions 8 to 13 are combined and concentrated to dryness at 50° C. under reduced pressure (30 mm Hg; 4 kPa) to give 10 -[(2RS)-1-piperidino-2-propyl]-2-phenothiazinecarbonitrile (13.6 g).

Workup

  1. temperatureto reflux for 19 hours
  2. temperatureAfter cooling
  3. washthe mixture is washed with distilled water (6×150 cc)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness at 50° C. under reduced pressure (30 mm Hg; 4 kPa)
  7. customThe residue is purified by chromatography on a column (height: 96 cm; diameter: 4.8 cm) of silica gel (0.06-0.2 mm)
  8. washeluting with 90:10, 85:15, 80:20 and 75:25 (by volume)
  9. customrespectively) of cyclohexane and ethyl acetate and collecting 500- cc fractions
  10. concentrationconcentrated to dryness at 50° C. under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-758168ee664c4937b8a1b16659bb50f2
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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