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

HRID 1834862
Notes
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Reaction equation

HRID 1834862 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 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 241
Benzene
Solvent
HCID 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. Anal. Calc'd. for C22H19F4N .HCl: C, 64.48; H, 4.92; Cl, 8.65. Found: C, 64.75; H, 4.89; Cl, 8.64.

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-4130ae4f8c3347b38e05bb46299b29d1
Source dataset
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04071570

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes