4-Toluenesulfonyl chloride → 4-n-Propyl-2-toluene-p-sulphonyloxymethylmorpholine

HRID 1283106Notes

Reaction equation

HRID 1283106 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][CH3:11])[CH2:4]1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH2:9]([N:5]1[CH2:6][CH2:7][O:8][CH:3]([CH2:2][O:1][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])[CH2:4]1)[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 214304252-Hydroxymethyl-4-n-propylmorpholine

Product 1

HCID 214303624-n-Propyl-2-toluene-p-sulphonyloxymethylmorpholineYield 11.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

2-Hydroxymethyl-4-n-propylmorpholine (16.2 g.) is dissolved in dry pyridine (50 ml.) and a solution of toluene-p-sulphonylchloride (21.4 g.) in dry pyridine (50 ml.) is added dropwise with stirring. The mixture is stirred at 20°-25°C. for 3 hours. The pyridine is removed under reduced pressure, water (100 ml.) is added to the residue and the product is extracted into ether (3 × 150 ml.). The ethereal solution is washed with water, dried (MgSO4), filtered and the ether evaporated to give 4-n-propyl-2-toluene-p-sulphonyloxymethylmorpholine (3.6 g.) as an oil which forms a hydrochloride, m.p. 172°-173°C. on recrystallisation from methanol/ether.

Workup

  1. stirringThe mixture is stirred at 20°-25°C. for 3 hours
  2. customThe pyridine is removed under reduced pressure, water (100 ml.)
  3. additionis added to the residue
  4. extractionthe product is extracted into ether (3 × 150 ml.)
  5. washThe ethereal solution is washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe ether evaporated

Sources & evidence

ORD record
ord-0265d609ba9746089baa4edbd83b8eb3
Source dataset
uspto-grants-1976_08
Patent number
US03974158

Reaction notes

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