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

HRID 2085395Notes

Reaction equation

HRID 2085395 reaction equation
C(O)(C(F)(F)F)=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

TFA (1.0 mL) was added to a solution of tert-butyl N-(3-{4-[3-(acetyl-amino)phenyl]piperidino}propyl)carbamate (340 mg) in dry dichloromethane (10 mL) and stirred at room temperature for 5 h. A 10% aqueous solution of KOH was added to the reaction mixture until pH >6 and then the dichloromethane was removed in vacuo. The aqueous layer was frozen and lyophilized, giving a solid which was then extracted with methanol. Removal of methanol gave the desired product (120 mg) as an oil. 1H NMR δ 8.56-8.46 (s, 1H), 7.43-7.30 (m, 2H), 7.23-7.16 (apparent t, 1H, J=7.5 Hz), 6.95-6.92 (m, 1H), 3.03-2.99 (m, 2H), 2.77-2.73 (t, 2H, J=6.6 Hz), 2.50-1.60 (m, 10 H), 2.13 (s, 3 H).

Workup

  1. customthe dichloromethane was removed in vacuo
  2. temperatureThe aqueous layer was frozen
  3. customgiving a solid which
  4. extractionwas then extracted with methanol
  5. customRemoval of methanol

Sources & evidence

ORD record
ord-1f45597d4b474ae2b757470ba7fb7983
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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