Trifluoroacetic acid → 1-(3-Fluoro-5-trifluoromethyl-benzyl)-piperidin-4-ylamine

HRID 1258149Notes

Reaction equation

HRID 1258149 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(C)(C)C.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:19]Br.C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:23]=1)[CH2:19][N:11]1[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 27375751-(Bromomethyl)-3-fluoro-5-(trifluoromethyl)benzene

Product 1

HCID 532561571-(3-Fluoro-5-trifluoromethyl-benzyl)-piperidin-4-ylamineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of piperidin-4-ylcarbamic acid tert-butyl ester (4 g, 20 mmol), 3-fluoro-5-(trifluoromethyl)benzyl bromide (4.6 g, 18.1 mmol) and diisoproylethylamine (4.7 ml, 27.1 mmol) in dichloromethane (25 ml) was stirred at room temperature for 2 h. After this period, trifluoroacetic acid (32 ml) was added and the reaction mixture was stirred for a further 2 h. The solvent was evaporated in vacuo and a saturated solution of sodium carbonate was added. The mixture was extracted with dichloromethane and the separated organic layer was dried (Na2SO4), filtered, and the solvent evaporated in vacuo to yield D7 (4 g, 80%) as a solid. C13H16F4N2 requires 276. Found 277 (MH+)

Workup

  1. waitAfter this period
  2. stirringthe reaction mixture was stirred for a further 2 h
  3. customThe solvent was evaporated in vacuo
  4. additiona saturated solution of sodium carbonate was added
  5. extractionThe mixture was extracted with dichloromethane
  6. dry with materialthe separated organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-faaca458ac754415acae0d218db4530c
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

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