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

HRID 1607745

반응식

HRID 1607745 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

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-diaminhexanoate 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.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureUpon cooling
  4. custommethyl 2,5-diaminhexanoate 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

출처 및 근거

ORD 기록
ord-6cb7627b6c384bcc96650ac41c9eddf1
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04866206

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