Benzylamine → Diethyl 3-benzylamino-2-pentenedioate

HRID 1649693

Reaction equation

HRID 1649693 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=[O:5].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:15]([NH:22][C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 66045Diethyl acetonedicarboxylate

Product 1

HCID 70353029Diethyl 3-benzylamino-2-pentenedioateYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50.00 g (0.247 mol) of diethyl acetonedicarboxylate was added dropwise 31.79 g (0.297 mol) of benzylamine at such a rate that reaction temperature was kept below 50° C. The reaction mixture was stirred at room temperature for 12 hours and poured into H2O, extracted twice with ether, dried (MgSO4) and concentrated in vacuo affording 60.00 g of a yellow-green oil. Crude was purified by HPLC using 10% ethyl acetate/cyclohexane affording 46.2 g of a yellow semi solid. This was kugelrohr distilled at 53 Pa and collected at a pot temperature of 148°-150° C. to give 39.4 g (55%) of enamine diester as a beige crystalline solid; mp 34°-36° C.

Workup

  1. customthat reaction temperature
  2. customwas kept below 50° C
  3. extractionextracted twice with ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e7425a1245f4cabb6063452b2f58e88
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Linked notes

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