Toluene → HCID 12899757, compound

HRID 2291152Notes

Reaction equation

HRID 2291152 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:18])[CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23]Cl.[H-].[Na+].C1(C)C=CC=CC=1>O>[CH3:19][N:20]([CH2:21][CH2:22][CH2:23][O:18][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:25]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 12899756HCID 12899756, compound

Product 1

HCID 12899757HCID 12899757, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g of 1-(p-fluorophenyl)-4-phenyl-1-butanol, 10 g of γ-dimethylaminopropyl chloride, 2.0 g of sodium hydride (65%) and 100 ml of toluene was heated under refluxing for 30 minutes. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on silica gel to give 1-[3-(N,N-dimethylamino)propoxy]-1-(p-fluorophenyl)-4-phenylbutane. M.P., 80°-83° C. (fumarate).

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 30 minutes
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-121128aef871446fad8f5d25cd84e697
Source dataset
uspto-grants-1986_10
Patent number
US04620036

Reaction notes

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