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

HRID 2396618Notes

Reaction equation

HRID 2396618 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-7892a3b60d684a24bc8fa5271006f985
Source dataset
uspto-grants-1996_02
Patent number
US05492954

Reaction notes

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