Dibenzylamine → (E)-N,N,N',N'-tetrabenzylbut-2-enediamide

HRID 1404342

Reaction equation

HRID 1404342 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](Cl)(=[O:22])/[CH:17]=[CH:18]/[C:19](Cl)=[O:20]>C(Cl)Cl>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:16](=[O:22])/[CH:17]=[CH:18]/[C:19]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 5325504Fumaryl chloride

Product 1

HCID 86722949(E)-N,N,N',N'-tetrabenzylbut-2-enediamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−5° C.) solution of N,N-dibenzylamine (19.3 mL, 100 mmol) in DCM (200 mL) is added TEA (13.8 mL, 100 mmol). To this solution is added, drop wise over 5 minutes, fumaroyl chloride (4.2 mL, 40 mmol). On complete addition, the cold bath is removed and stirring continued for 1 hr. This solution is diluted with DCM, washed with HCl (approx. 100 mL of 1M aq.) then water (2×), dried over MgSO4 and concentrated. The solid residue is crystallized from hot (109° C.) toluene to give the title compound (17.9 g) as a white solid. ESI-MS (m/z) 475 (MH)+.

Workup

  1. additionTo this solution is added
  2. additionOn complete addition
  3. customthe cold bath is removed
  4. waitcontinued for 1 hr
  5. additionThis solution is diluted with DCM
  6. washwashed with HCl (approx. 100 mL of 1M aq.)
  7. dry with materialwater (2×), dried over MgSO4
  8. concentrationconcentrated
  9. customThe solid residue is crystallized from hot (109° C.) toluene

Sources & evidence

ORD record
ord-873f164e835244a9ae247159ab8e4c78
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Linked notes

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