Ethanol → 5-[1-Hydroxy-2-[[2-(2-methoxyphenoxy)ethyl]amino]ethyl]-2-methylbenzenesulfonamide

HRID 1855960Notes

Reaction equation

HRID 1855960 reaction equation
[OH:1][CH:2]([C:23]1[CH:24]=[CH:25][C:26]([CH3:33])=[C:27]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:28]=1)[CH2:3][N:4]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])CC1C=CC=CC=1.C(O)C>CO.[H][H].[Pd]>[OH:1][CH:2]([C:23]1[CH:24]=[CH:25][C:26]([CH3:33])=[C:27]([S:29]([NH2:32])(=[O:30])=[O:31])[CH:28]=1)[CH2:3][NH:4][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]

Participants

6

Reactant 2

HCID 702EthanolHCID 133583145-(2-{Benzyl[2-(2-methoxyphenoxy)ethyl]amino}-1-hydroxyethyl)-2-methylbenzene-1-sulfonamide

Product 1

HCID 21695-[1-Hydroxy-2-[[2-(2-methoxyphenoxy)ethyl]amino]ethyl]-2-methylbenzenesulfonamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

In 200 ml of methanol was dissolved 20 g of 5-{1-hydroxy-2-[N-benzyl-2-(2-methoxyphenoxy)ethylamino]ethyl}-2-methylbenzenesulfonamide. After adding thereto 20 ml of ethanol containing about 10% hydrogen chloride and 1 g of 10% palladium charcoal, the mixture was shaked in hydrogen gas stream. When the absorption of hydrogen stopped, the catalyst was filtered away and the filtrate was distilled off under reduced pressure. The residue was dissolved in 100 ml of ethanol while it was hot and the solution was allowed to stand overnight in ice chamber, whereby 12.8 g of the α-type crystals of 5-{1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]-ethyl}-2-methylbenzenesulfonamide were obtained as the colorless crystals. The physical and chemical properties of the product were as follows:

Workup

  1. additionAfter adding
  2. customWhen the absorption of hydrogen
  3. filtrationthe catalyst was filtered away
  4. distillationthe filtrate was distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in 100 ml of ethanol while it

Sources & evidence

ORD record
ord-43d754f7cda44e6aac8a7c2969dc6aa6
Source dataset
uspto-grants-1980_08
Patent number
US04217305

Reaction notes

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