Ethylenediamine → 2-{3-[(2-Aminoethyl)amino]-2-hydroxypropoxy}benzamide

HRID 2058671Notes

Reaction equation

HRID 2058671 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH:8]1[O:10][CH2:9]1)(=[O:3])[NH2:2].[CH2:15]([NH2:18])[CH2:16][NH2:17]>>[C:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH:8]([OH:10])[CH2:9][NH:17][CH2:16][CH2:15][NH2:18])(=[O:3])[NH2:2]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 12548678HCID 12548678, compound

Product 1

HCID 204785302-{3-[(2-Aminoethyl)amino]-2-hydroxypropoxy}benzamide

Procedure

1-(o-Carbamoylphenoxy)-2,3-epoxypropane (20 g.) is added to ethylenediamine (125 ml.) and the mixture is stirred at laboratory temperature for 1 hour and then evaporated to dryness under reduced pressure. The residue is stirred with water (150 ml.), the mixture is filtered and the filtrate is evaporated to dryness under reduced pressure. The residue is crystallised from acetonitrile and there is thus obtained a residue 1-(o-carbamoylphenoxy)-3-(β-aminoethyl)aminopropan-2-ol, m.p. 91°-93° C.

Workup

  1. customevaporated to dryness under reduced pressure
  2. stirringThe residue is stirred with water (150 ml.)
  3. filtrationthe mixture is filtered
  4. customthe filtrate is evaporated to dryness under reduced pressure
  5. customThe residue is crystallised from acetonitrile and there

Sources & evidence

ORD record
ord-551ac81883254c2f8dc7524b5ff16d1c
Source dataset
uspto-grants-1982_03
Patent number
US04318921

Reaction notes

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