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

HRID 1461412Notes

Reaction equation

HRID 1461412 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-propylamine 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 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 of benzene each
  7. dry with materialThe benzene solution is dried
  8. customevaporated

Sources & evidence

ORD record
ord-19da264f11cd4ad28a71986b271d143c
Source dataset
uspto-grants-1991_12
Patent number
US05075338

Reaction notes

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