Benzaldehyde → Methyl 2-benzylideneaminohexanoate

HRID 1008753Notes

Reaction equation

HRID 1008753 reaction equation
C(N(CC)CC)C.S([O-])([O-])(=O)=O.[Mg+2].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.[NH2:23][CH:24]([CH2:29][CH2:30][CH2:31][CH3:32])[C:25]([O:27][CH3:28])=[O:26]>ClCCl>[CH:14](=[N:23][CH:24]([CH2:29][CH2:30][CH2:31][CH3:32])[C:25]([O:27][CH3:28])=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 14039064Methyl norleucinate--hydrogen chloride (1/1)

Product 1

HCID 23074255Methyl 2-benzylideneaminohexanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (8.67 g) (supplied from Wako Pure chemical Industries), 7.74 g of magnesium sulfate anhydrate and 4.55 g of benzaldehyde were added to a suspension of 7.79 g of methyl 2-aminohexanoate hydrochloride in 70 mL of dichloromethane, and stirred at room temperature overnight. The reaction suspension was filtrated, and the filtrate was concentrated. Then 280 mL of ether was added to the residue. The resulting suspension was filtrated and the filtrate was concentrated. Again 280 mL of ether was added to the residue, and the filtration and the concentration were repeated in the same manner, to yield 10.0 g of the title compound.

Workup

  1. filtrationThe reaction suspension was filtrated
  2. concentrationthe filtrate was concentrated
  3. additionThen 280 mL of ether was added to the residue
  4. filtrationThe resulting suspension was filtrated
  5. concentrationthe filtrate was concentrated
  6. additionAgain 280 mL of ether was added to the residue
  7. filtrationthe filtration
  8. concentrationthe concentration

Sources & evidence

ORD record
ord-00193568fc4a4a99800949f3fe36318f
Source dataset
uspto-grants-2011_07
Patent number
US07973030B2

Reaction notes

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