p-Toluenesulfonic acid monohydrate → Ethyl 1-benzyl-4-(4-chloro-2-(3-ethoxy-3-oxoprop-1-ynyl)phenyl)piperidine-4-carboxylate

HRID 1868815Notes

Reaction equation

HRID 1868815 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[C:26]#[C:27][C:28](OCC)([O:32]CC)[O:29][CH2:30][CH3:31])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO.O>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[C:26]#[C:27][C:28]([O:29][CH2:30][CH3:31])=[O:32])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67099667Ethyl 1-benzyl-4-(4-chloro-2-(3,3,3-triethoxyprop-1-ynyl)phenyl)piperidine-4-carboxylate

Product 1

HCID 67099889Ethyl 1-benzyl-4-(4-chloro-2-(3-ethoxy-3-oxoprop-1-ynyl)phenyl)piperidine-4-carboxylateYield 91.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 1-benzyl-4-(4-chloro-2-(3,3,3-triethoxyprop-1-ynyl)phenyl)piperidine-4-carboxylate (820 mg, 1.5 mmol) and p-toluenesulfonic acid monohydrate (443 mg, 2.3 mmol) in EtOH (25 mL) and water (5 mL) was stirred at 23° C. After 30 minutes, the solvents were removed in vacuo, and the residue was diluted with EtOAc (200 mL) and washed with 10% HCl solution (100 mL), saturated NaHCO3 solution (100 mL) and brine (100 mL), dried over MgSO4, and concentrated in vacuo affording 620 mg of ethyl 1-benzyl-4-(4-chloro-2-(3-ethoxy-3-oxoprop-1-ynyl)phenyl)piperidine-4-carboxylate. MS m/e=454.1 (M+H)+.

Workup

  1. customthe solvents were removed in vacuo
  2. additionthe residue was diluted with EtOAc (200 mL)
  3. washwashed with 10% HCl solution (100 mL), saturated NaHCO3 solution (100 mL) and brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84dbb1075cb44160bba2df8a119e5bd7
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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