Diethylamine → HCID 54515869, compound

HRID 1728411Notes

Reaction equation

HRID 1728411 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[O:6]1[CH2:10][CH:7]1[CH:8]=[CH2:9]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:3]([CH2:9][CH:8]=[CH:7][CH2:10][OH:6])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 13586Vinyloxirane

Product 1

HCID 54515869HCID 54515869, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.4 g of polymer-bound triphenylphosphine palladium(0) from Aldrich Chemical Co., Inc., Milwaukee, Wisconsin, Catalogue No. 24815-0 was suspended in 20 ml of THF, followed by 1.42 ml (14.3 mmol) diethylamine and 1.15 ml (14.3 mmol) 3,4-epoxy-1-butene. The reaction mixture was stirred at room temperature for 36 hours. The catalyst was removed by filtration and the filtrate was concentrated by evaporation at reduced pressure. The residue was distilled at reduced pressure. The reaction resulted in an 80% yield of 4-(N,N-diethylamino)-2-buten-1-ol. None of the isomeric 1,2 adduct was detected. The increased ratio of 4-(N,N-diethylamino)-2-buten-1-ol produced as compared to the approximately 1:1 ratio seen in Example 1 (with an unbound catalyst) has tremendous manufacturing advantages when extrapolated out to production scale synthesis.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated by evaporation at reduced pressure
  3. distillationThe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-343f2cf2078947319b6aa46fb870df95
Source dataset
uspto-grants-1994_07
Patent number
US05326873

Reaction notes

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