Trifluoroacetic acid → [4-(4-Fluoro-benzyloxy)-phenyl]-(3-methyl-butyl)-piperidin-4-yl-amine

HRID 2299906Notes

Reaction equation

HRID 2299906 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[CH:22][CH:21]=2)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([N:14]([CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:25][CH:24]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 544663194-{[4-(4-Fluorobenzyloxy)-phenyl]-(3-methyl-butyl)-amino}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 18380604[4-(4-Fluoro-benzyloxy)-phenyl]-(3-methyl-butyl)-piperidin-4-yl-amineYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{[4-(4-fluorobenzyloxy)-phenyl]-(3-methyl-butyl)-amino}-piperidine-1-carboxylic acid tert-butyl ester (If, 1.80 g, 3.82 mmol) was dissolved in CH2Cl2 (12 mL), treated with TFA (12 mL), and stirred for 20 minutes. The reaction was concentrated and placed under vacuum for 20 minutes, then diluted with EtOAc (200 mL), washed twice with saturated sodium bicarbonate solution and once with brine, dried over Na2SO4, and concentrated to give 0.89 g (74%) of the desired product.

Workup

  1. concentrationThe reaction was concentrated
  2. waitplaced under vacuum for 20 minutes
  3. additiondiluted with EtOAc (200 mL)
  4. washwashed twice with saturated sodium bicarbonate solution and once with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-85a643c30c1448399dc45592fcd82645
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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