Trifluoroacetic acid → 2-((3-chlorophenyl)((R)-piperidin-3-yl)methoxy)-N-ethylacetamide

HRID 451659Notes

Reaction equation

HRID 451659 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]([O:29][CH2:30][C:31]([NH:33][CH2:34][CH3:35])=[O:32])[C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)[CH:12]=[CH:13][CH:14]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]([C@@H:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[O:29][CH2:30][C:31]([NH:33][CH2:34][CH3:35])=[O:32])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59201433(3R)-tert-butyl 3-((3-chlorophenyl)(2-(ethylamino)-2-oxoethoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 592014532-((3-chlorophenyl)((R)-piperidin-3-yl)methoxy)-N-ethylacetamideYield 912.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of TFA in CH2Cl2 (20% v/v, 5 mL) was added (3R)-tert-butyl 3-((3-chlorophenyl)(2-(ethylamino)-2-oxoethoxy)methyl)piperidine-1-carboxylate (57.9 mg, 0.0141 mmol). The reaction was monitored by tlc (elution solvent: 5:1 petroleum ether/EtOAc). When the reaction was complete, the mixture was washed with satd aq NaHCO3 and water, dried over Na2SO4 and concentrated to give 2-((3-chlorophenyl)((R)-piperidin-3-yl)methoxy)-N-ethylacetamide (40 mg, 91%). MS (E/Z): 311 (M+H+).

Workup

  1. washThe reaction was monitored by tlc (elution solvent: 5:1 petroleum ether/EtOAc)
  2. washthe mixture was washed with satd aq NaHCO3 and water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1f5f849cd88844c6b4c5b11d782c351e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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