Hydrochloric Acid → HCID 67459883, compound

HRID 554106Notes

Reaction equation

HRID 554106 reaction equation
O1CCCC1.B.[CH3:7][C:8]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH2:12])=O.[ClH:21]>O1CCCC1>[ClH:21].[CH3:7][C:8]1[C:16]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:14]=[CH:13][C:9]=1[CH2:10][NH2:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 27755662-methyl-3-(trifluoromethyl)benzamide

Product 1

HCID 67459883HCID 67459883, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Borane tetrahydrofuran (1M, 39.4 ml, 39.4 mmol) was added to a solution of 2-methyl-3-trifluoromethyl benzamide (2 g, 9.85 mmol) in tetrahydrofuran (75 ml) and stirred at 70° C. for 5 hrs. LCMS showed incomplete reaction so heating at 70° C. under argon was continued overnight and then for a further 5 hrs following this. The reaction mixture was treated with 2N aqueous hydrogen chloride and stirred at 100° C. for 4 hrs and then left to cool over the weekend. The mixture was reduced to dryness undervacuum and then partitioned between dichloromethane and 2N aqueous sodium hydroxide. The organic layer was separated using a hydrophobic frit and reduced to give a residue which was purified by flash silica column chromatography (eluting with 0-5% 2N ammonia/methanol in dichloromethane). The solvent was evaporated and the residue taken up in diethyl ether and treated with 1M ethereal hydrogen chloride. The solid that precipitated was collected by filtration and this was then triturated with dichloromethane and after filtration 2-Methyl-3-(trifluoromethyl)phenyl]methyl}amine hydrochloride (1.4 g) was obtained as a white solid.

Workup

  1. customreaction
  2. temperatureso heating at 70° C. under argon
  3. waitwas continued overnight
  4. waitfor a further 5 hrs following
  5. stirringstirred at 100° C. for 4 hrs
  6. waitleft
  7. temperatureto cool over the weekend
  8. custompartitioned between dichloromethane and 2N aqueous sodium hydroxide
  9. customThe organic layer was separated
  10. customto give a residue which
  11. customwas purified by flash silica column chromatography (eluting with 0-5% 2N ammonia/methanol in dichloromethane)
  12. customThe solvent was evaporated
  13. additiontreated with 1M ethereal hydrogen chloride
  14. customThe solid that precipitated
  15. filtrationwas collected by filtration
  16. customthis was then triturated with dichloromethane
  17. filtrationafter filtration 2-Methyl-3-(trifluoromethyl)phenyl]methyl}amine hydrochloride (1.4 g)
  18. customwas obtained as a white solid

Sources & evidence

ORD record
ord-e91cb27254cb4c469053b97a644e52e7
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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