p-Toluenesulfonic acid monohydrate → 1-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde tosylate

HRID 1620492Notes

Reaction equation

HRID 1620492 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=[O:13])[CH2:8][CH2:7]1.O.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[S:31]([C:28]1[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=1)([OH:34])(=[O:33])=[O:32].[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde

Product 1

HCID 866786841-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde tosylateYield 95.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (170 mg) in toluene (2 mL) was added p-toluenesulfonic acid monohydrate (95 mg), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate. The obtained solid was dried at 60° C. under reduced pressure to give the title compound (244 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was washed with ethyl acetate
  3. customThe obtained solid was dried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-0a7ee7149e3d424690dc321f91ccbc96
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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