2-Amino-1-(4-benzyloxyphenyl)ethanol → HCID 53959586, compound

HRID 1462356Notes

Reaction equation

HRID 1462356 reaction equation
CC1(C)[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([O:13][CH2:14][C:15](=O)[CH3:16])[CH:11]=[CH:12][C:4]=2[O:3]1.C(O[C:27]1[CH:36]=[CH:35][C:30]([CH:31]([OH:34])[CH2:32][NH2:33])=[CH:29][CH:28]=1)C1C=CC=CC=1.[H][H]>CO>[C:6]([C:5]1[CH:9]=[C:10]([CH:11]=[CH:12][C:4]=1[OH:3])[O:13][CH2:14][CH:15]([NH:33][CH2:32][CH:31]([OH:34])[C:30]1[CH:35]=[CH:36][CH:27]=[CH:28][CH:29]=1)[CH3:16])(=[O:8])[NH2:7]

Participants

5

Reactant 3

HCID 4239902-Amino-1-(4-benzyloxyphenyl)ethanolHCID 137543322,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 53959586HCID 53959586, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 9.6 g of 2,3-dihydro-2,2-dimethyl-6-(2-oxo-propoxy)-4H-1,3-benzoxazin-4-one and 9.37 g of 4-benzyloxy-α-(aminomethyl)benzyl alcohol in 250 ml of methanol is hydrogenated analogously to Example 1 until one equivalent of hydrogen has been taken up. The catalyst is filtered off and, after adding 40 ml of isopropylamine, the solution is refluxed for 1 hour. Evaporation of the reaction mixture yields 4-benzyloxy-α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-1-methyl-ethyl]-aminomethyl-benzyl alcohol in the form of a crystalline mass which can be hydrogenated without further purification.

Workup

  1. filtrationThe catalyst is filtered off
  2. additionafter adding 40 ml of isopropylamine
  3. temperaturethe solution is refluxed for 1 hour
  4. customEvaporation of the reaction mixture

Sources & evidence

ORD record
ord-054b35ec5d1e4bcfb8ee98c07ce1bf54
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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