2-Amino-1-(4-benzyloxyphenyl)ethanol → 4-benzyloxy-alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol

HRID 1462359Notes

Reaction equation

HRID 1462359 reaction equation
[NH2:1][CH2:2][CH:3]([OH:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.Br[CH2:20][CH2:21][O:22][C:23]1[CH:24]=[CH:25][C:26]2[O:31]C(C)(C)[NH:29][C:28](=[O:34])[C:27]=2[CH:35]=1>>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([CH:3]([OH:18])[CH2:2][NH:1][CH2:20][CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([OH:31])=[C:27]([C:28](=[O:34])[NH2:29])[CH:35]=2)=[CH:5][CH:6]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 4239902-Amino-1-(4-benzyloxyphenyl)ethanolHCID 137544136-(2-Bromoethoxy)-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

Product 1

HCID 541676984-benzyloxy-alpha-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol

Procedure

A mixture of 21 g of α-(aminomethyl)-4-benzyloxybenzyl alcohol and 12 g of 6-(2-bromoethoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one is stirred in an oil bath at 130° for 1 hour. The reaction mixture is partitioned between 500 ml of ethyl acetate and 50 ml of 2N aqueous ammonia solution, the organic phase is separated off and evaporated and the residue is recrystallised from isopropanol. 4-Benzyloxy-α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol with a melting point of 160°-162° is obtained.

Workup

  1. customThe reaction mixture is partitioned between 500 ml of ethyl acetate and 50 ml of 2N aqueous ammonia solution
  2. customthe organic phase is separated off
  3. customevaporated
  4. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-cc76c75f99254711af56e75a59fbb1d5
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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