Hydrochloric Acid → HCID 69342993, compound

HRID 855321Notes

Reaction equation

HRID 855321 reaction equation
[CH3:1][C:2]([C:7]1[CH:27]=[CH:26][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=O)=[CH:9][CH:8]=1)([CH3:6])[CH2:3][CH2:4][CH3:5].Cl.[OH-].[Na+]>C1COCC1>[CH3:6][C:2]([C:7]1[CH:27]=[CH:26][C:10]([CH2:11][NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=2)=[CH:9][CH:8]=1)([CH3:1])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 693428514-(1,1-dimethyl-butyl)-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

Product 1

HCID 69342993HCID 69342993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 440 mg of 4-(1,1-dimethyl-butyl)-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (1.17 mmol) in 10 ml of THF was added dropwise to 4.66 ml of a 1 molar solution of BH3-THF complex in THF at 0° C. The reaction mixture was stirred for 1 h at rt and then heated to reflux overnight. Upon cooling to rt 2 ml of 6N HCl were added and the mixture was stirred for 1 h. Then the pH was adjusted to 9 by addition of 1 N sodium hydroxide solution and the mixture was extracted three times with EtOAc. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. This gave 422 mg (100%) of [4-(1,1-dimethyl-butyl)-benzyl]-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine as a light yellow oil which was used in the following coupling step without further purification. MS (ISP) 364.2 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. additionwere added
  4. stirringthe mixture was stirred for 1 h
  5. extractionthe mixture was extracted three times with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThis gave 422 mg (100%) of [4-(1,1-dimethyl-butyl)-benzyl]-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine as a light yellow oil which was used in the following coupling step without further purification

Sources & evidence

ORD record
ord-ea9478f329a24169978942cf703cb33f
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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