Benzylamine → HCID 89315947, compound

HRID 526730Notes

Reaction equation

HRID 526730 reaction equation
[CH3:1][N:2](C)/[CH:3]=[CH:4]/[C:5](=[O:11])[CH:6]([O:9][CH3:10])[O:7][CH3:8].C(N)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH2:1]([NH:2]/[CH:3]=[CH:4]/[C:5](=[O:11])[CH:6]([O:9][CH3:10])[O:7][CH3:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 5709580((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamine

Product 1

HCID 89315947HCID 89315947, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (11 g, 63.5 mmol) and benzylamine (6.94 ml, 63.5 mmol) in toluene (130 ml) was stirred under reflux for 4 hours. Evaporated to dryness under vacuum, the residue was applied on a column, eluted with petroleum ether-ethyl acetate mixture 3:1, fractions collected to give (E)-4-(benzylamino)-1,1-dimethoxybut-3-en-2-one (6.4 g, 27.2 mmol, 42.8% yield) as dark yellow oil.

Workup

  1. temperatureunder reflux for 4 hours
  2. customEvaporated to dryness under vacuum
  3. washeluted with petroleum ether-ethyl acetate mixture 3:1, fractions
  4. customcollected

Sources & evidence

ORD record
ord-1691e1954e5c43c9930555a7994cbb9c
Source dataset
uspto-grants-2016_05
Patent number
US09346751B2

Reaction notes

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