4-Toluenesulfonyl chloride → HCID 86642833, compound

HRID 1667742Notes

Reaction equation

HRID 1667742 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1995763-Morpholino-1-propanol

Product 1

HCID 86642833HCID 86642833, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a mixture of 0.145 g (1 mmole) of 3-morpholin-4-yl-propan-1-ol and 5 mL of pyridine was added 0.001 g of 4-dimethylaminopyridine and 0.210 g (1.1 mmole) of p-toluenesulphonyl chloride. The mixture was stirred at ambient temperature overnight and then concentrated under reduced pressure. The residue was taken up in 10 mL of dichloromethane and washed once with 5 mL of saturated sodium bicarbonate, twice with 5 mL of water, and then brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.22 g of toluene-4-sulfonic acid 3-morpholin-4-yl-propyl ester as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed once with 5 mL of saturated sodium bicarbonate, twice with 5 mL of water
  3. dry with materialbrine, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de674a5056af457d9787694d61336d81
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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