Phenylethanolamine → alpha-(((4,5-Dihydro-1H-imidazol-2-yl)amino)methyl)benzyl alcohol

HRID 1576839

Reaction equation

HRID 1576839 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][NH2:4].N([C:15]1[NH:16][CH2:17][CH2:18][N:19]=1)[N+]([O-])=O.C1(C)C(C)=CC=CC=1>CC(C)=O>[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][NH:4][C:15]1[NH:19][CH2:18][CH2:17][N:16]=1

Participants

5

Reactant 3

HCID 1000PhenylethanolamineHCID 7237O-XyleneHCID 4100422-Nitroamino-2-imidazoline

Product 1

HCID 103775alpha-(((4,5-Dihydro-1H-imidazol-2-yl)amino)methyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 15.8 parts β-hydroxy-phenethyl-amine, 13 parts 2-nitramino-2-imidazoline and 8 parts xylene is stirred and heated for 30 minutes at 160°C. (oil-bath). After cooling the reaction mixture to a temperature of about 70°C., there are added 40 parts acetone. The whole is filtered warm and after cooling the filtrate to room temperature, the precipicated product is filtered off and dried, yielding 2-(β-hydroxy-phenethyl-amino)-2-imidazoline; m.p. 147°-149°C.

Workup

  1. temperatureAfter cooling the reaction mixture to a temperature of about 70°C., there
  2. filtrationThe whole is filtered
  3. temperaturewarm
  4. temperatureafter cooling the filtrate to room temperature
  5. filtrationthe precipicated product is filtered off
  6. customdried

Sources & evidence

ORD record
ord-89c90c3b4a1241ecba9222bfc6b6ec7a
Source dataset
uspto-grants-1976_09
Patent number
US03983133

Linked notes

Loading…