Hydrochloric Acid → 4-[2-(2-Hydroxy-2-phenylethylamino)ethoxy]phenylacetamide hydrochloride

HRID 275453Notes

Reaction equation

HRID 275453 reaction equation
C([N:8]([CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH2:30])=[O:29])=[CH:23][CH:22]=1)[CH2:9][CH:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C1C=CC=CC=1.CCOCC.[ClH:36]>CC(O)C.C(O)(=O)C.[Pd].C(OCC)(=O)C>[ClH:36].[OH:17][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][NH:8][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH2:30])=[O:29])=[CH:23][CH:22]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 117419734-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide

Product 1

HCID 189972404-[2-(2-Hydroxy-2-phenylethylamino)ethoxy]phenylacetamide hydrochloride

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A preformed solution of 4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide in propan-2-ol and glacial acetic acid (see below) was hydrogenated in the presence of 10% w/w palladium on carbon (1.0 g) at about 20 bar and 60° C. for 12 hours. The mixture was cooled, filtered and the filtrate was evaporated under reduced pressure. The residual oil thus obtained was dissolved in ethyl acetate and treated with a solution of ether saturated with hydrogen chloride. The precipitated solid was crystallised from methanol to give 4-[2-(2-hydroxy-2-phenylethylamino)-ethoxy]phenylacetamide hydrochloride (6.8 g), m.p. 250°-251° C. (softens at about 248° C.); microanalysis: found C, 61.2; H, 6.5; N, 8.3; Cl, 10.3%; required for C18H23ClN2O3 : C, 61.6; H, 6.6; N, 8.0; Cl, 10.1%.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residual oil thus obtained
  5. customThe precipitated solid was crystallised from methanol

Sources & evidence

ORD record
ord-37d1c04858d5451db22943e62410c7ba
Source dataset
uspto-grants-1995_02
Patent number
US05393779

Reaction notes

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