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

HRID 1426377Notes

Reaction equation

HRID 1426377 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]=[CH:22][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]=[CH:22][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 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 180021391-[(3,4-Difluorophenyl)methyl]piperidin-4-amineYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of piperidin-4-ylcarbamic acid tert-butyl ester (5 g, 25.0 mmol), 3,4-difluorobenzyl bromide (4.7 g, 22.7 mmol) and diisoproylethylamine (5.9 ml, 34.0 mmol) in dichloromethane (50 ml) was stirred at room temperature for 2 h. After this period, trifluoroacetic acid (31 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 D7 (5.2 g, 93%) as a solid. C12H16F2N2 requires 226. Found 227 (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-b6661e76cced4cdabbe830d747c6376a
Source dataset
uspto-grants-2015_01
Patent number
US08933101B2

Reaction notes

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