Tyramine → HCID 12541329, compound

HRID 373976Notes

Reaction equation

HRID 373976 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:11]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:12]1[O:14][CH2:13]1>CS(C)=O>[OH:14][CH:12]([CH2:11][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 5610TyramineHCID 31217Phenyl glycidyl ether

Product 1

HCID 12541329HCID 12541329, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4.0 g of tyramine and 5.25 g of phenyl glycidyl ether in 100 ml of dimethylsulfoxide was heated to 100°60 for 17 hours. The solvent was evaporated in vacuo and the residue was chromatographed on 400 g of silica gel. 4.3 g of p-[2-[bis[(RS)-2-hydroxy-3-phenoxypropyl]amino]ethyl]phenol was firstly eluted with chloroform/n-propanol/concentrated ammonia (1000:10:1) as an amorphous substance, ε218 =20710. The further fractions yielded 4.2 g of pure (RS)-p-[2-[(2-hydroxy-3-phenoxypropyl) amino]ethyl]phenol of m.p. 122°-124°, ε221 =15310.

Workup

  1. temperaturewas heated to 100°60 for 17 hours
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was chromatographed on 400 g of silica gel
  4. wash4.3 g of p-[2-[bis[(RS)-2-hydroxy-3-phenoxypropyl]amino]ethyl]phenol was firstly eluted with chloroform/n-propanol/concentrated ammonia (1000:10:1) as an amorphous substance, ε218 =20710

Sources & evidence

ORD record
ord-d5a9afe0adf14113b42c277ee3a6c21e
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

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