HCID 22063482, compound → HCID 11632691, compound

HRID 1666162Notes

Reaction equation

HRID 1666162 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:36])[CH2:21][NH:22][C:23]([CH3:35])([CH3:34])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:36])[CH2:21][NH:22][C:23]([CH3:34])([CH3:35])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([CH:31]([CH3:32])[CH3:33])=[CH:29][CH:30]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1

Participants

4

Reactant 1

HCID 22063482HCID 22063482, compound

Product 1

HCID 11632691HCID 11632691, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.6 g (3.0 mmol) of 6-benzyloxy-8-{1-hydroxy-2-[2-(4-isopropylphenyl)-1,1-dimethylethylamino]ethyl}-4H-benzo[1,4]oxazin-3-one is dissolved in methanol and hydrogenated with palladium on charcoal as catalyst at normal pressure and ambient temperature. The catalyst is suction filtered, the solvent distilled off, and the residue recrystallized from isopropanol. White solid. Yield: 1.1 g (85%, hydrochloride); melting point 248° C.-250° C.; mass spectrometry: [M+H]+=399.

Workup

  1. filtrationfiltered
  2. distillationthe solvent distilled off
  3. customthe residue recrystallized from isopropanol

Sources & evidence

ORD record
ord-1364d4a1cf1248e3ac7f4fad91da7d76
Source dataset
uspto-grants-2011_10
Patent number
US08044046B2

Reaction notes

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