Propylamine → 1-Phenyl-N-propyl-2-pentanamine

HRID 1588093Notes

Reaction equation

HRID 1588093 reaction equation
[CH2:1]([C:8]([CH2:10][CH2:11][CH3:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([NH2:16])[CH2:14][CH3:15].[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C1C=CC=CC=1.CO.O>[CH2:13]([NH:16][CH:8]([CH2:10][CH2:11][CH3:12])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:14][CH3:15]

Participants

8

Reactant 4

HCID 7852PropylamineHCID 811881-Phenyl-2-pentanoneHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 102623691-Phenyl-N-propyl-2-pentanamine

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

11.0 g (0.068 mole) of benzyl-propyl-ketone are dissolved in 110 ml of benzene, whereupon 8.0 g (0.135 mole) of n-propyl-amine and 22.6 g (0.2 mole) of anhydrous calcium chloride are added to the solution. The reaction mixture is stirred at 40°-50° C. for 6 hours, then filtered and evaporated. The crude ketimine thus obtained is dissolved in 120 ml of methanol, whereupon 6.4 g (0.17 mole) of sodium borohydride are added. The reaction mixture is allowed to stand, whereupon it is poured into 500 ml of water and extracted five times with 100 ml of benzene each. The benzene solution is dried and evaporated. The crude N-propyl-1-phenyl-2-pentylamine thus obtained is purified by distillation in vacuo. B.p.: 112°-120° C./7 Hgmm, n20D =1.5030.

Workup

  1. additionare added to the solution
  2. filtrationfiltered
  3. customevaporated
  4. customThe crude ketimine thus obtained
  5. additionare added
  6. extractionextracted five times with 100 ml of benzene each
  7. dry with materialThe benzene solution is dried
  8. customevaporated

Sources & evidence

ORD record
ord-7b014c98301d4471b32a4fb4be330de4
Source dataset
uspto-grants-1993_06
Patent number
US05220068

Reaction notes

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