Benzaldehyde → Methyl 2,6-bis(benzylideneamino)hexanoate

HRID 1252555

Reaktionsgleichung

Reaktionsgleichung von HRID 1252555
Cl.N[CH:3]([CH2:7][CH2:8][CH2:9][CH2:10]N)[C:4](O)=O.Cl.Cl.Cl.[NH2:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])[C:17]([O:19][CH3:20])=[O:18].[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:34](N(CC)CC)C>CO.C(Cl)Cl>[CH:4](=[N:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:17]([O:19][CH3:20])=[O:18])[C:3]1[CH:34]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

8

Edukt 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12047Lysine hydrochloride, DL-HCID 13661416Methyl DL-lysinate dihydrochloride

Produkt 1

HCID 14231031Methyl 2,6-bis(benzylideneamino)hexanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A suspension of 2,6-diaminohexanoic acid hydrochloride (18.26 g, 100 mmol) in dry methanol (100 ml) is saturated with gaseous hydrochloric acid and heated under reflux for 2 hours. Upon cooling, methyl 2,5-diaminohexanoate dihydrochloride crystallizes. To an ice cooled suspension of methyl 2,6-diaminohexanoate dihydrochloride (4.66 g, 20 mmol) in methylene chloride (50 ml) is added benzaldehyde (4.04 g, 40 mmol) and then dropwise a solution of triethylamine (4.24 g, 40 mmol) in methylene chloride (30 ml). The reaction mixture is allowed to stand overnight at room temperature under stirring and is then concentrated under reduced pressure to give a residue which is extracted into ether (diethyl ether). The ether extract is washed with water and brine, dried over MgSO4, and concentrated to give methyl 2,6-bis(benzylideneamino)hexanoate as an oily residue.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureUpon cooling
  4. custommethyl 2,5-diaminohexanoate dihydrochloride crystallizes
  5. temperatureTo an ice cooled
  6. concentrationis then concentrated under reduced pressure
  7. customto give a residue which
  8. extractionis extracted into ether (diethyl ether)
  9. extractionThe ether extract
  10. washis washed with water and brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c1887996564d4518896d2558cccebfc2
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743691

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