4-Toluenesulfonyl chloride → 4-Piperidinol, 1-methyl-, 4-(4-methylbenzenesulfonate)

HRID 1533873Notes

Reaction equation

HRID 1533873 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.C(N(CC)CC)C>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 660484-Piperidinol, 1-methyl-

Product 1

HCID 2873334-Piperidinol, 1-methyl-, 4-(4-methylbenzenesulfonate)Yield 72.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

1-Methyl-4-piperidyl para-toluenesulphonate may be obtained in the following manner: para-toluenesulphonyl chloride (19.60 g) is added in the course of approximately 1 hour 30 minutes to a solution, cooled to 0° C., of 4-hydroxy-1-methylpiperidine (11.50 g) in pyridine (50 cc), and the mixture is stirred for 4 hours at 0° C. and then 12 hours at a temperature in the region of 20° C. After the addition of triethylamine (14.10 g) and stirring for a further 15 minutes, distilled water (300 cc) and ethyl acetate (300 cc) are added. The aqueous phase is separated after settling has taken place and washed with ethyl acetate (200 cc). The organic extracts are combined, washed with distilled water (500 cc in total), dried over anhydrous magnesium sulphate and evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the region of 45° C. The final traces of pyridine are removed under a higher vacuum (0.1 mm Hg; 13.5 Pa). 1-Methyl-4-piperidyl para-toluenesulphonate (19.6 g) is thereby obtained in the form of a brown oil [Rf=0.56; thin-layer chromatography on silica; eluent: acetonitrile/ammonia solution (d=0.92) (95:5 by volume)].

Workup

  1. custom12 hours
  2. customin the region of 20° C
  3. stirringstirring for a further 15 minutes
  4. distillationdistilled water (300 cc) and ethyl acetate (300 cc)
  5. additionare added
  6. customThe aqueous phase is separated after settling
  7. washwashed with ethyl acetate (200 cc)
  8. washwashed with distilled water (500 cc in total)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. customevaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the region of 45° C
  11. customThe final traces of pyridine are removed under a higher vacuum (0.1 mm Hg; 13.5 Pa)

Sources & evidence

ORD record
ord-4e5ce349d5254dbdbafa80c3edb2528d
Source dataset
uspto-grants-1992_02
Patent number
US05086051

Reaction notes

Loading…