N-(4-Methanesulphonamidophenacyl)-N-methyl-benzylamine → 2-Hydroxy-N-methyl-2-(4-methanesulphonamidophenyl)ethylamine

HRID 1607112Notes

Reaction equation

HRID 1607112 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:23]=[CH:22][C:9]([C:10](=[O:21])[CH2:11][N:12](CC2C=CC=CC=2)[CH3:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3]>C(O)C.[Pd]>[OH:21][CH:10]([C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:23][CH:22]=1)[CH2:11][NH:12][CH3:13]

Participants

4

Reactant 1

HCID 19898951N-(4-Methanesulphonamidophenacyl)-N-methyl-benzylamine

Product 1

HCID 119542852-Hydroxy-N-methyl-2-(4-methanesulphonamidophenyl)ethylamineYield 37.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(4-Methanesulphonamidophenacyl)-N-methyl-benzylamine (14.5 g) in ethanol (300 ml) containing 10% palladium on charcoal (2.0 g) was stirred under a hydrogen atmosphere (50 psi) at room temperature for 18 hours. Further catalyst (1.0 g) was added and hydrogenation was continued for a further 18 hours. The reaction was filtered and evaporated to afford an oil which was chromatographed on silica [Merck `Kieselgel 60` (trade Mark)], eluting with methylene chloride containing methanol (0% up to 20%) to give, after collection and evaporation of appropriate fractions, the title compound as a solid, yield 5 g. [Washing the column with methylene chloride:methanol:acetic acid (80:20:0.25) gave a further 4 g of the product as the acetate salt].

Workup

  1. waithydrogenation was continued for a further 18 hours
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. customto afford an oil which
  5. customwas chromatographed on silica [Merck `Kieselgel 60` (trade Mark)],
  6. washeluting with methylene chloride
  7. additioncontaining methanol (0% up to 20%)
  8. customto give
  9. customafter collection and evaporation of appropriate fractions
  10. wash[Washing the column with methylene chloride:methanol:acetic acid (80:20:0.25)

Sources & evidence

ORD record
ord-61d4d13308674f098d5191d6ff880f69
Source dataset
uspto-grants-1989_09
Patent number
US04863948

Reaction notes

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