Methane → 4-Chloro-N,N-diethylbenzenebutanamine

HRID 464026Notes

Reaction equation

HRID 464026 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:4][CH:3]=1.C.[H][H]>C(O)(=O)C.[Pt]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 20263609(E)-4-(4-Chlorophenyl)-N,N-diethyl-2-buten-1-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 139715264-Chloro-N,N-diethylbenzenebutanamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

Add 2.0 g (0.0084 mole) of (E)-4-(4-chlorophenyl)-N,N-diethyl-2-buten-1-amine to flask containing 0.20 g platinum (5%) on activated charcoal suspended in 15 ml glacial acetic acid. Stir reaction mixture under one atmosphere hydrogen until hydrogen absorption ceases (41/2 hours). Filter reaction mixture with methylene chloride wash and 50 ml distilled water. Separate layers and extract aqueous with 3×70 ml methylene chloride. Combine methylene chloride extracts and wash with cold 2×75 ml 1N NaOH. Dry organic layer over MgSO4, filter and evaporate to yield the title compound.

Workup

  1. customuntil hydrogen absorption ceases (41/2 hours)
  2. filtrationFilter
  3. customreaction mixture with methylene chloride
  4. washwash
  5. distillation50 ml distilled water
  6. extractionSeparate layers and extract aqueous with 3×70 ml methylene chloride
  7. washCombine methylene chloride extracts and wash with cold 2×75 ml 1N NaOH
  8. filtrationDry organic layer over MgSO4, filter
  9. customevaporate

Sources & evidence

ORD record
ord-1cbc1d42900041cba3d17d261d475a1c
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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