Hydrochloric Acid → N-Benzyl-2-(alpha,alpha,beta,beta-tetrafluorophenethyl)benzylamine

HRID 1284276Notes

Reaction equation

HRID 1284276 reaction equation
[F:1][C:2]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH2:16])([F:12])[C:3]([F:11])([F:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.C1C=CC=CC=1>[CH2:21]([NH:16][CH2:15][C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[C:2]([F:12])([F:1])[C:3]([F:11])([F:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 203722482-(alpha,alpha,beta,beta-Tetrafluorophenethyl)benzylamine

Product 1

HCID 20372253N-Benzyl-2-(alpha,alpha,beta,beta-tetrafluorophenethyl)benzylamine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A mixture of 3.9 g. (0.0138 mole) of 2-(α,α,β,β -tetrafluorophenethyl)benzylamine, 1.77 g. (0.014 mole) of benzyl chloride, 2.5 g. of anhydrous potassium carbonate, and 25 ml. of benzene is stirred and heated to refluxing for about 40 hours. After filtration, the solvent is evaporated under reduced pressure, leaving the product as the residual oil. Purification is effected by column chromatography on 250 g. of silica, the product being eluted with 1% methanol in chloroform. The fractions that show one spot of rf 0.7 on a fluorescent silica thin layer plate developed with 5% methanol in chloroform are combined. Evaporation of the solvent under reduced pressure leaves the product as the residual oil. The base is converted to the hydrochloride salt by treating an ethanolic solution with a slight excess of 8N hydrogen chloride in ethanol. Dilution with absolute ether precipitates the hydrochloride as white crystals, m.p. 188°-189.5°C. Recrystallization from acetone yields a purified sample, m.p. 188.5°-190°C.

Workup

  1. additionA mixture of 3.9 g
  2. temperatureheated
  3. temperatureto refluxing for about 40 hours
  4. filtrationAfter filtration
  5. customthe solvent is evaporated under reduced pressure
  6. customleaving the product as the residual oil
  7. customPurification
  8. washof silica, the product being eluted with 1% methanol in chloroform
  9. customEvaporation of the solvent under reduced pressure
  10. customleaves the product as the residual oil
  11. customDilution with absolute ether precipitates the hydrochloride as white crystals, m.p. 188°-189.5°C
  12. customRecrystallization from acetone
  13. customyields a purified sample, m.p. 188.5°-190°C.

Sources & evidence

ORD record
ord-5ebb9b43ecb94f7ea505448ad0bef5e7
Source dataset
uspto-grants-1976_08
Patent number
US03978127

Reaction notes

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