Toluene → 2-Amino-1-[3-(4-phenylpiperidin-1-yl)pyrrolidin-1-yl]ethanone

HRID 406469Notes

Reaction equation

HRID 406469 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:27])[N:10]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[CH2:11]1)(C)(C)C.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[NH2:7][CH2:8][C:9]([N:10]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:16][CH2:17][CH:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:19][CH2:20]2)[CH2:11]1)=[O:27]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 59764640{2-Oxo-2-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 597646952-Amino-1-[3-(4-phenylpiperidin-1-yl)pyrrolidin-1-yl]ethanoneYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {2-oxo-2-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethyl}-carbamic acid tert-butyl ester (preparation #10) (3.25 g, 8.39 mmol) in DCM (200 mL) was added TFA (15 mL). The reaction mixture was stirred at ambient temperature for about 5 h. Toluene (100 mL) was added and the solvents were removed in vacuo. The residue was dissolved in DCM (400 mL) and the organic was washed with saturated NaHCO3, 1.0N NaOH, brine, dried over MgSO4, filtered and concentrated in vacuo to give 2-amino-1-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethanone (2.34 g, 97%) as a light tan solid; RP-HPLC (Table 1, Method a) Rt 1.09 min; m/z: (M+H)+ 288.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe residue was dissolved in DCM (400 mL)
  3. washthe organic was washed with saturated NaHCO3, 1.0N NaOH, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d722e188075147e18a2098c6de752165
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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