Water → 4-tosyloxymethyl-N-(4-nitrophenyl)piperidine

HRID 538012Notes

Reaction equation

HRID 538012 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>N1C=CC=CC=1>[S:24]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 23448266(1-(4-Nitrophenyl)piperidin-4-yl)methanol

Product 1

HCID 866606684-tosyloxymethyl-N-(4-nitrophenyl)piperidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 4-hydroxymethyl-N-(4-nitrophenyl)piperidine (47.3 g, 200 mmol) obtained in Example 4(1) was dissolved in pyridine (300 ml), and p-toluenesulfonyl chloride (45.8 g, 240 mmol) was added thereto under ice-cooling, followed by stirring for 4 hours. Water was added to the reaction mixture, and the precipitate was collected by filtration. The obtained solid was dried under reduced pressure, thereby obtaining 4-tosyloxymethyl-N-(4-nitrophenyl)piperidine (72.7 g, 93%) as a yellow solid.

Workup

  1. temperatureunder ice-cooling
  2. filtrationthe precipitate was collected by filtration
  3. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-e6e2e1ebccea4044976e26bd89bbe783
Source dataset
uspto-grants-2014_10
Patent number
US08865714B2

Reaction notes

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