4-Toluenesulfonyl chloride → 4-Benzyl-2-toluene-p-sulphonyloxymethylmorpholine

HRID 1283001Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4-benzyl-2-hydroxymethylmorpholine (118.8 g.) in dry pyridine (250 ml.) toluene-p-sulphonyl chloride (120.2 g.) is added gradually at 18°-25°C. The mixture is stirred for 20 hours at ambient temperature (ca. 20°C.) and the pyridine is removed under diminished pressure. The residue is diluted with water, the mixture made alkaline by the addition of sodium hydroxide solution, and the product is then extracted into ether. The ethereal solution is dried (MgSO4) and filtered, the ether is evaporated and the residual solid is crystallised from cyclohexane or petroleum ether (b.p. 60°-80°C.) to give 4-benzyl-2-toluene-p-sulphonyloxymethylmorpholine, m.p. 78°-79°C.

Workup

customthe pyridine is removed under diminished pressure
additionThe residue is diluted with water
additionby the addition of sodium hydroxide solution
extractionthe product is then extracted into ether
dry with materialThe ethereal solution is dried (MgSO4)
filtrationfiltered
customthe ether is evaporated
customthe residual solid is crystallised from cyclohexane or petroleum ether (b.p. 60°-80°C.)

Sources & evidence

ORD record: ord-868b08044b9a40a0b83e58f0135b3be7
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03974156

Reaction notes

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