Dicyclohexylcarbodiimide → N,N-dimethyl-2-benzyl-3-(4-trifluoromethylphenoxy)-propylamine oxalate

HRID 621609Notes

Reaction equation

HRID 621609 reaction equation
[CH2:1]([CH:8]([CH2:11][N:12]([CH3:14])[CH3:13])[CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[F:30][C:31]([F:40])([F:39])[C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1.O.O.[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45]>CCOCC>[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45].[CH3:13][N:12]([CH2:11][CH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][O:10][C:35]1[CH:36]=[CH:37][C:32]([C:31]([F:40])([F:39])[F:30])=[CH:33][CH:34]=1)[CH3:14]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 61373Oxalic acid dihydrateHCID 678744-(Trifluoromethyl)phenolHCID 136539342-Benzyl-3-(dimethylamino)propan-1-ol

Product 1

HCID 13653936N,N-dimethyl-2-benzyl-3-(4-trifluoromethylphenoxy)-propylamine oxalate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A mixture of 2-benzyl-3-dimethylaminopropanol (4.2 g), dicyclohexylcarbodiimide (4.6 g) and cuprous chloride (0.2 g) is maintained at 80° for 40 hours. 4-Trifluoromethylphenol (5.0 g) is added, and the mixture maintained at 130° for 12 hours. The reaction mixture is cooled and ether (100 ml) is added. The insoluble material is filtered off and the filtrate extracted with 2N hydrochloric acid (3×100 ml). The acidic solutions are combined and made basic by the addition of concentrated aqueous ammonia. The aqueous solution is extracted with ether (3×150 ml), and the combined extracts dried over magnesium sulfate and evaporated under reduced pressure to give the ether as a yellow oil. This material is converted to the oxalate salt by dissolving in ether and adding the calculated quantity of oxalic acid dihydrate in ether. Filtration gives N,N-dimethyl-2-benzyl-3-(4-trifluoromethylphenoxy)propylamine oxalate, m.p. 147°-149°.

Workup

  1. temperatureis maintained at 80° for 40 hours
  2. temperaturethe mixture maintained at 130° for 12 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationThe insoluble material is filtered off
  5. extractionthe filtrate extracted with 2N hydrochloric acid (3×100 ml)
  6. additionmade basic by the addition of concentrated aqueous ammonia
  7. extractionThe aqueous solution is extracted with ether (3×150 ml)
  8. dry with materialthe combined extracts dried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customto give the ether as a yellow oil
  11. filtrationFiltration

Sources & evidence

ORD record
ord-3370858c99014b55b6ec31f8ebad61e0
Source dataset
uspto-grants-1989_04
Patent number
US04824868

Reaction notes

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