Benzyl acetone → 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]-o-anisamide

HRID 866778

Reaction equation

HRID 866778 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([O:14][CH3:15])=[CH:7][CH:6]=1)[OH:4].[CH2:16]([CH2:23][C:24](=O)[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H][H]>C(O)C.[Pt]>[OH:4][CH:3]([C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([O:14][CH3:15])=[CH:7][CH:6]=1)[CH2:2][NH:1][CH:24]([CH3:25])[CH2:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 17355Benzyl acetoneHCID 203185835-(2-Amino-1-hydroxyethyl)-o-anisamideHCID 178418361HCID 178418361, compound

Product 1

HCID 203185875-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]-o-anisamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of the above 5-(2-amino-1-hydroxyethyl)-o-anisamide in ethanol (70ml) was added benzyl acetone (1.5g), and the mixture was gently refluxed for 1 hour. The cooled solution was then added to a suspension of pre-reduced 5% platinum on charcoal (0.4g) in ethanol (10 ml) and hydrogenated until uptake was complete. Hydrogen uptake was complete within 14 hours. The catalyst and solvent were removed to leave 5-[1-hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]-o-anisamide as an oil (2.36g) which slowly crystallised on rubbing with ether, m.p. 110°-148°.

Workup

  1. temperaturethe mixture was gently refluxed for 1 hour
  2. customThe catalyst and solvent were removed

Sources & evidence

ORD record
ord-2e8c743f4f4c4ba6909a6b3e551855d0
Source dataset
uspto-grants-1978_07
Patent number
US04101579

Linked notes

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