Trifluoroacetic acid → N-{3-[1-(3-amino propyl)4-piperidinyl]phenyl}acetamide

HRID 1269147

Reaction equation

HRID 1269147 reaction equation
FC(F)(F)C(O)=O.[C:8]([NH:11][C:12]1[CH:13]=[C:14]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)[CH2:20][CH2:19]2)[CH:15]=[CH:16][CH:17]=1)(=[O:10])[CH3:9].[OH-].[K+]>ClCCl>[NH2:27][CH2:26][CH2:25][CH2:24][N:21]1[CH2:22][CH2:23][CH:18]([C:14]2[CH:13]=[C:12]([NH:11][C:8](=[O:10])[CH3:9])[CH:17]=[CH:16][CH:15]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 22049023Tert-butyl 3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propylcarbamate

Product 1

HCID 21957249N-{3-[1-(3-amino propyl)4-piperidinyl]phenyl}acetamideYield 48.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.0 mL) was added to a solution of tert-butyl 3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propylcarbamate (340 mg) in dry dichloromethane (10 mL) and the reaction mixture was stirred at room temperature for 5 h. The reaction mixture was basified to pH 12 by addition of a 10% aqueous solution of KOH and then the dichloromethane was removed in vacuo. The aqueous layer was frozen and lyophilized to give a solid, which was extracted with methanol. Removal of the solvent gave the desired product (120 mg) as an oil: 1H NMR (400 MHz, CDCl3) δ 7.48 (m, 1H), 7.38 (d, 1H, J=7.7 Hz), 7.24 (t, 1H, J=7.7 Hz), 6.99 (d, 1H, J=7.7 Hz), 3.11 (d, 2H, J=11.6 Hz), 2.84 (t, 2H, J=6.6 Hz), 2.59–2.52 (m, 1H), 2.50 (t, 2H, J=6.6 Hz), 2.18–2.09 (m, 2H), 2.13 (s, 3H), 1.90–1.72 (m, 6H).

Workup

  1. customthe dichloromethane was removed in vacuo
  2. temperatureThe aqueous layer was frozen
  3. customto give a solid, which
  4. extractionwas extracted with methanol
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-4d8b9902a4e746109ba825a9bab28d71
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Linked notes

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