(1S,2R)-(+)-Norephedrine → alpha-[1-(2-Imidazolin-2-ylamino)ethyl]benzyl alcohol

HRID 1576841

Reaction equation

HRID 1576841 reaction equation
[NH2:1][CH:2]([CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:3].N([C:16]1[NH:17][CH2:18][CH2:19][N:20]=1)[N+]([O-])=O.C1(C)C(C)=CC=CC=1>CC(C)=O>[NH:20]1[CH2:19][CH2:18][N:17]=[C:16]1[NH:1][CH:2]([CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:3]

Participants

5

Reactant 3

HCID 4786(1S,2R)-(+)-NorephedrineHCID 7237O-XyleneHCID 4100422-Nitroamino-2-imidazoline

Product 1

HCID 54133258alpha-[1-(2-Imidazolin-2-ylamino)ethyl]benzyl alcohol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.5 parts of α-(1-aminoethyl)benzyl alcohol (also known as morephedrine), 5.2 parts of 2-(nitramino)-2-imidazoline and 8 parts of xylene is stirred for 30 minutes while heating at 160°-170°C. The reaction mixture is cooled and diluted with acetone. The latter is removed in vacuo, yielding α-[1-(2-imidazolin-2-ylamino)-ethyl]benzyl alcohol as an oily residue.

Workup

  1. temperaturewhile heating at 160°-170°C
  2. temperatureThe reaction mixture is cooled
  3. customThe latter is removed in vacuo

Sources & evidence

ORD record
ord-7b3aeac0763840eb994f97a3f570e980
Source dataset
uspto-grants-1976_09
Patent number
US03983133

Linked notes

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