HCID 13338482, compound → HCID 13338491, compound

HRID 2417996Notes

Reaction equation

HRID 2417996 reaction equation
[ClH:1].C([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH3:21])=[CH:12][CH:11]=1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[ClH:1].[CH3:21][NH:20][CH2:19][CH2:18][CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([OH:9])=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 13338482HCID 13338482, compound

Product 1

HCID 13338491HCID 13338491, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-benzyloxy-4-(3-methylaminopropoxy)benzene hydrochloride (8.4 g) in acetic acid (250 ml) was hydrogenated over 0.5 g of 10% palladium on carbon in a Parr apparatus (50°; initial pressure 50 psi). The reaction was completed within 0.4 hours and after the catalyst was removed by filtration, the solvent was distilled in vacuo. The residue was crystallized from methanol-ethyl acetate to give 4.8 g (80% of 4-(3-methylaminopropoxy)phenol hydrochloride, mp 167°-169°.

Workup

  1. custom50°
  2. customafter the catalyst was removed by filtration
  3. distillationthe solvent was distilled in vacuo
  4. customThe residue was crystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-2482e319fdc44b73a9b10dd9a33dabe4
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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