Trifluoroacetic acid → 4-[1-(2-Dimethylamino-acetyl)-piperidin-4-yl]-phenylamine

HRID 1989063Notes

Reaction equation

HRID 1989063 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:25])[CH2:21][N:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:15][CH2:16][N:17]([C:20](=[O:25])[CH2:21][N:22]([CH3:23])[CH3:24])[CH2:18][CH2:19]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68679986{4-[1-(2-Dimethylamino-acetyl)-piperidin-4-yl]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 686774374-[1-(2-Dimethylamino-acetyl)-piperidin-4-yl]-phenylamineYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{4-[1-(2-Dimethylamino-acetyl)-piperidin-4-yl]-phenyl}-carbamic acid tert-butyl ester (0.72 mmol) was diluted in CH2Cl2 (3 mL) and TFA (3 mL) was added. After 1 h, the reaction mixture was concentrated. Water (2 mL) was added and the solution was frozen and lyophilized overnight to provide (0.11 g) (59%) of 1-[4-(4-amino-phenyl)-piperidin-1-yl]-2-dimethylamino-ethanone. 1H NMR (TFA salt) (400 MHz, CDCl3) δ (ppm): 10.54 (s, 1H), 7.52 (d, 2H, J=8.5 Hz), 7.20 (d, 2H, J=8.5 Hz), 4.10 (s, 2H), 3.34-3.37 (m, 2H), 2.97-3.12 (m, 3H), 2.85 (s, 6H), 1.88-1.91 (m, 2H), 1.69-1.78 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionWater (2 mL) was added
  3. temperaturethe solution was frozen
  4. waitlyophilized overnight

Sources & evidence

ORD record
ord-7cb9c871bf27456a83367c5a227b33cd
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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