Trifluoroacetic acid → 1-[(3,5-Difluorophenyl)methyl]piperidin-4-amine

HRID 1258147Notes

Reaction equation

HRID 1258147 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:24])[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]([F:24])[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 5188963,5-Difluorobenzyl bromideHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 221824001-[(3,5-Difluorophenyl)methyl]piperidin-4-amineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of piperidin-4-ylcarbamic acid tert-butyl ester (5 g, 24.9 mmol), 3,5-difluorobenzyl bromide (2.9 ml, 22.7 mmol) and diisoproylethylamine (5.9 ml, 34.03 mmol) in dichloromethane (50 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 layers were dried (Na2SO4), filtered, and the solvent evaporated in vacuo to yield D5 (4.5 g, 90%) as a solid. C12H16F2N2 requires 226. Found 227 (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 layers were dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-ecc59bcfadf046a190ad4b58c8285c18
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

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