1-Phenoxy-2-propanamine → 1-(1-Methyl-2-phenoxyethylamino)-3-(4-hydroxyphenoxy)-2-propanol

HRID 1156519Notes

Reaction equation

HRID 1156519 reaction equation
[O:1]1[CH2:12][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH3:13][CH:14]([NH2:23])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:13][CH:14]([NH:23][CH2:12][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 370871-Phenoxy-2-propanamineHCID 128749844-(2,3-Epoxy-1-propoxy)-phenol

Product 1

HCID 128557431-(1-Methyl-2-phenoxyethylamino)-3-(4-hydroxyphenoxy)-2-propanol

Procedure

A mixture of 1.66 g. (10 mmole) of 4-(2,3-epoxy-1-propoxy)-phenol and 4.5 g. (30 mmole) of 1-methyl-2-phenoxyethylamine was heated at 90° C. for 3 hours. The residue was triturated with ether and filtered. Recrystallization from ethyl acetate to which a little methanol was added gave 1-(1-methyl-2-phenoxyethylamino)-3-(4-hydroxyphenoxy)-2-propanol; mp 173°-175° C.

Workup

  1. additionA mixture of 1.66 g
  2. customThe residue was triturated with ether
  3. filtrationfiltered
  4. customRecrystallization from ethyl acetate to which a little methanol
  5. additionwas added

Sources & evidence

ORD record
ord-6d8498f4a1da4aca9773ea4034d9707e
Source dataset
uspto-grants-1982_06
Patent number
US04336261

Reaction notes

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