Dibenzylamine → 1-Acetoxy-4-dibenzylamino-2-butene

HRID 2255813Notes

Reaction equation

HRID 2255813 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]([O:19][CH2:20][CH:21]=[CH:22][CH2:23]OC(=O)C)(=[O:18])[CH3:17]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([O:19][CH2:20][CH:21]=[CH:22][CH2:23][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:18])[CH3:17]

Participants

5

Reactant 2

HCID 7656DibenzylamineHCID 1404022-Butene-1,4-diol diacetate

Product 1

HCID 537897791-Acetoxy-4-dibenzylamino-2-butene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of dibenzylamine (40 g, 0.2 mol) and 2-butene-1,4-diol diacetate (105 g, 0.61 mol) dissolved in 150 ml of tetrahydrofuran (THF) is treated with tetrakis(triphenylphosphine)palladium (0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and the excess 2-butene-1,4-diol diacetate is removed by bulb-to-bulb distillation at 80°-90° C./1 mm. The residue is purified by eluting through a short plug of silica gel (1:1 ethyl acetate: hexanes). 1-Acetoxy-4-dibenzylamino-2-butene is obtained in a yield of 59.2 g (95%).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe excess 2-butene-1,4-diol diacetate is removed by bulb-to-bulb distillation at 80°-90° C./1 mm
  3. customThe residue is purified
  4. washby eluting through a short plug of silica gel (1:1 ethyl acetate: hexanes)

Sources & evidence

ORD record
ord-77b3faf5406a42c4906943ef135b916c
Source dataset
uspto-grants-1993_08
Patent number
US05240976

Reaction notes

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