Trifluoroacetic acid → 1-(3,4,5-Trifluoro-benzyl)-piperidin-4-ylamine

HRID 1258150Notes

Reaction equation

HRID 1258150 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]([F:25])[C:23]=1[F:24])[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]([F:25])[C:23]=1[F:24])[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 27770623,4,5-Trifluorobenzyl bromide

Product 1

HCID 532561891-(3,4,5-Trifluoro-benzyl)-piperidin-4-ylamineYield 105.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of piperidin-4-ylcarbamic acid tert-butyl ester (2.5 g, 12.4 mmol), 3,4,5-trifluorobenzyl bromide (2.5 g, 11.3 mmol) and diisoproylethylamine (2.9 ml, 16.9 mmol) in dichloromethane (25 ml) was stirred at room temperature for 2 h. After this period, trifluoroacetic acid (15.6 ml) was added and the reaction 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 layers were dried (Na2SO4), filtered, and the solvent evaporated in vacuo to yield D8 (2.9 g, 96%) as a solid. C12H15F3N2 requires 244. Found 245 (MH+)

Workup

  1. waitAfter this period
  2. stirringthe reaction 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 layers were dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-db277315753a4a08b644d327092ada98
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

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