Hydrochloric Acid → 4-(Trifluoromethyl)cyclohexan-1-amine hydrochloride

HRID 2060870Notes

Reaction equation

HRID 2060870 reaction equation
C([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:11][CH2:10]1)C1C=CC=CC=1.[ClH:19]>CO.O1CCOCC1.[Pd]>[ClH:19].[F:16][C:15]([F:17])([F:18])[CH:12]1[CH2:11][CH2:10][CH:9]([NH2:8])[CH2:14][CH2:13]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 43434579Benzyl(4-trifluoromethylcyclohexyl)amine

Product 1

HCID 187699224-(Trifluoromethyl)cyclohexan-1-amine hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of benzyl(4-trifluoromethylcyclohexyl)amine (Preparation 4) (1.48 g, 5.73 mmol) in MeOH (150 mL) was passed through an H-Cube at 100° C. fitted with a 10% Pd/C CatCart and on full H2 mode. The volume was reduced to 50 mL and 4M HCl in dioxane (1.43 mL) was added. The precipitate was filtered, the filtrate collected and the solvent removed in vacuo. The resulting residue was triturated with acetone to give the title compound: δH (CD3OD) 1.41-1.53 (4H, m), 2.03-2.25 (5H, m), 3.07-3.15 (1H, m).

Workup

  1. customwas passed through an H-Cube at 100° C.
  2. additionwas added
  3. filtrationThe precipitate was filtered
  4. customthe filtrate collected
  5. customthe solvent removed in vacuo
  6. customThe resulting residue was triturated with acetone

Sources & evidence

ORD record
ord-2d9a4257b37e4839b42c5275f1a5e409
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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