Phenylethanolamine → N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-hydroxy-2-phenylethanamine

HRID 434377Notes

Reaction equation

HRID 434377 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][NH2:4].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](=O)[CH3:23])=[CH:17][CH:16]=1)([O:13][CH3:14])=[O:12].CCOCC>C(O)C.[Pd]>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:23])=[CH:17][CH:16]=1)([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 1000PhenylethanolamineHCID 3283Diethyl EtherHCID 11137970Methyl 4-(2-oxopropyl)benzoate

Product 1

HCID 6917725N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-hydroxy-2-phenylethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-hydroxy-2-phenylethanamine (17.7 g) and 1-(4-carbomethoxyphenyl) propan-2-one (24.8 g) in ethanol (300 ml) was refluxed for one hour. When cooled, 10% Pd/C (1.0 g) was added and the mixture was hydrogenated on a Parr Hydrogenator at 60° and 60 psi for six hours. The mixture was filtered and the filtrate was evaporated to an oil which was taken up in methanol (75 ml). The solution was allowed to stand at 4° to give crystals (Batch 1). Ether (75 ml) was added to the mother liquors to obtain subsequent crops (Batches 2 & 3). The mother liquors were evaporated to an oil, which was crystallised from ether (Batch 4).

Workup

  1. temperaturewas refluxed for one hour
  2. temperatureWhen cooled
  3. customwas hydrogenated on a Parr Hydrogenator at 60°
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated to an oil which
  6. customto stand at 4°
  7. customto give crystals (Batch 1)
  8. customto obtain subsequent crops (Batches 2 & 3)
  9. customThe mother liquors were evaporated to an oil, which
  10. customwas crystallised from ether (Batch 4)

Sources & evidence

ORD record
ord-995f7563b6c844b0836fa583cba53dd3
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

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