Trifluoroacetic acid → 1-{1-[4-(Trifluoromethyl)phenyl]piperidin-4-yl}methanamine

HRID 2093586Notes

Reaction equation

HRID 2093586 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)(C)(C)C>ClCCl>[F:30][C:28]([F:29])([F:31])[C:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:20][CH2:21][CH:16]([CH2:15][NH2:14])[CH2:17][CH2:18]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66853254Tert-butyl({1-[4-(trifluoromethyl)phenyl]piperidin-4-yl}methyl)carbamate

Product 1

HCID 595860101-{1-[4-(Trifluoromethyl)phenyl]piperidin-4-yl}methanamineYield 123.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trifluoroacetic acid (10 ml) and dichloromethane (10 ml) was added to tert-butyl({1-[4-(trifluoromethyl)phenyl]piperidin-4-yl}methyl)carbamate (1.36 g). This mixture was stirred at room temperature for 3 h. The sample was concentrated and taken up in dichloromethane (20 ml) and saturated aqueous sodium bicarbonate. The mixture was extracted and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title compound (1.21 g, 86%). Mass spectrum (ESI) 242.1 (M+1).

Workup

  1. concentrationThe sample was concentrated
  2. extractionThe mixture was extracted
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-071f88bfa2834bc49a00051e172efd00
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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