Ethanol → HCID 178479647, compound

HRID 2296349Notes

Reaction equation

HRID 2296349 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[ClH:7].C(=N)(OCC)[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)O.[CH2:21]([OH:23])C>>[ClH:7].[OH:23][C:21]1[N:1]([CH2:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][N:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1045PutrescineHCID 12387918Ethyl 2-hydroxy-2-phenylethanimidate--hydrogen chloride (1/1)

Product 1

HCID 178479647HCID 178479647, compoundYield 34%

Procedure

To 200 ml of absolute ethanol was added 1,4-diaminobutane at 0° C. with continuous stirring. To this solution waas added an equal molar amount of ethyl mandelimidate hydrochloride. After stirring at 0°-5° C. for two hours, the suspension was heated under reflux 12 hours then cooled and concentrated to remove any traces of NH3. The concentrated solution was acidified by dropwise addition of ethanolic HCl into the suspension which was then concentrated to dryness and the residue recrystallized several times from CH3CN/ether to yield 14.5 g (34%) of product: mp 179°-181° C. Structure was confirmed by IR and NMR.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux 12 hours
  3. temperaturethen cooled
  4. concentrationconcentrated
  5. customto remove any traces of NH3
  6. additionThe concentrated solution was acidified by dropwise addition of ethanolic HCl into the suspension which
  7. concentrationwas then concentrated to dryness
  8. customthe residue recrystallized several times from CH3CN/ether

Sources & evidence

ORD record
ord-cadabf6a12a44235b18e58b934466783
Source dataset
uspto-grants-1984_01
Patent number
US04428948

Reaction notes

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