4-Toluenesulfonyl chloride → HCID 13334364, compound

HRID 1252213Notes

Reaction equation

HRID 1252213 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][O:19][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13334363HCID 13334363, compound

Product 1

HCID 13334364HCID 13334364, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-p-nitrobenzyloxycarbonyl-4-hydroxymethylpiperidine (20 g) in dry pyridine (127 ml) was added p-toluenesulfonyl chloride (25.8 g) with ice-cooling, and the reaction mixture was kept overnight at the same temperature, diluted with ice water and extracted with diethyl ether dichloromethane. The extract was washed successively with water, dilute hydrochloric acid, aqueous sodium bicarbonate and again water, dried over anhydrous sodium sulfate and evaporated to give an oily residue which was crystallized from methanol to give N-p-nitrobenzyloxycarbonyl-4-p-toluenesulfonyloxymethylpiperidine.

Workup

  1. temperaturecooling
  2. extractionextracted with diethyl ether dichloromethane
  3. washThe extract was washed successively with water, dilute hydrochloric acid, aqueous sodium bicarbonate and again water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give an oily residue which
  7. customwas crystallized from methanol

Sources & evidence

ORD record
ord-0d1a5d8962cd4b898970a4295a873da7
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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