Benzaldehyde → Methyl 2-benzylideneaminohexanoate

HRID 970304Notes

Reaction equation

HRID 970304 reaction equation
Cl.[NH2:2][CH:3]([CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.S([O-])([O-])(=O)=O.[Mg+2].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[CH:25](=[N:2][CH:3]([CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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

To a suspension of 7.79 g of methyl 2-aminohexanoate hydrochloride in 70 ml of dichloromethane were added 8.67 g of triethylamine (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), 7.74 g of anhydrous magnesium sulfate, and 4.55 g of benzaldehyde and the resultant was stirred overnight at room temperature. The reaction suspension was then filtered and the filtrate was concentrated. 280 ml of ether was added to the residue and the resultant suspension was filtered and the filtrate was concentrated. Again, 280 ml of ether was added to the residue and filtration and concentration were similarly repeated to obtain 10.0 g of the title compound.

Workup

  1. filtrationThe reaction suspension was then filtered
  2. concentrationthe filtrate was concentrated
  3. addition280 ml of ether was added to the residue
  4. filtrationthe resultant suspension was filtered
  5. concentrationthe filtrate was concentrated
  6. additionAgain, 280 ml of ether was added to the residue and filtration and concentration

Sources & evidence

ORD record
ord-332311d18c5f4149a4c880390161ac35
Source dataset
uspto-grants-2007_12
Patent number
US07312208B2

Reaction notes

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