Water → 4-Phenyl-1-(p-tolylsulphonyl)piperidine-4-carbonitrile

HRID 1855653Notes

Reaction equation

HRID 1855653 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]1([C:18]2([C:24]#[N:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.O>ClCCl>[C:12]1([C:18]2([C:24]#[N:25])[CH2:19][CH2:20][N:21]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:22][CH2:23]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1811384-Piperidinecarbonitrile, 4-phenyl-

Product 1

HCID 905204-Phenyl-1-(p-tolylsulphonyl)piperidine-4-carbonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

17.2 g (89.8 mmol) of 4-methylbenzenesulfonyl chloride dissolved in 150 ml of dichloromethane are added to a solution of 20 g (89.8 mmol) of 4-phenylpiperidine-4-carbonitrile and 28 ml of triethylamine in 200 ml of dichloromethane. The reaction mixture is stirred for 1 hour at room temperature. The reaction is stopped by adding 200 ml of water, and is then extracted with dichloromethane. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then taken up in diethyl ether and filtered off. 30.3 g of 4-phenyl-1-(toluene-4-sulfonyl)piperidin-4-carbonitrile in the form of a white powder are obtained in a yield of 99%.

Workup

  1. extractionis then extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-2eaabe980f6749c8a46d93f8783977e9
Source dataset
uspto-grants-2015_02
Patent number
US08962846B2

Reaction notes

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