Trifluoroacetic acid → 1-[(1-Aminocyclopropyl)carbonyl]-5-(4-ethylphenyl)-N-phenylpiperidine-3-carboxamide

HRID 876271Notes

Reaction equation

HRID 876271 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH:20]([C:22](=[O:30])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][N:18]([C:31]([C:33]3([NH:36]C(=O)OC(C)(C)C)[CH2:35][CH2:34]3)=[O:32])[CH2:17]2)=[CH:12][CH:11]=1)[CH3:9]>ClCCl>[NH2:36][C:33]1([C:31]([N:18]2[CH2:17][CH:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:8][CH3:9])=[CH:11][CH:12]=3)[CH2:21][CH:20]([C:22]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:30])[CH2:19]2)=[O:32])[CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70854693tert-Butyl (1-{[3-(4-ethylphenyl)-5-(phenylcarbamoyl)piperidin-1-yl]carbonyl}cyclopropyl)carbamate

Product 1

HCID 667012711-[(1-Aminocyclopropyl)carbonyl]-5-(4-ethylphenyl)-N-phenylpiperidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon and at RT, 190 μl (2.5 mmol, 15 eq.) of trifluoroacetic acid were added to a solution of 81 mg (0.16 mmol) of tert-butyl (1-{[3-(4-ethylphenyl)-5-(phenylcarbamoyl)piperidin-1-yl]carbonyl}cyclopropyl)carbamate in 2 ml of dichloromethane. The reaction mixture was stirred at RT for 20 h, then concentrated under reduced pressure and repeatedly coevaporated with toluene. The crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 29 mg (45% of theory)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-1be291898c9d41edbaed942dcb6b2e4f
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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