Hydrochloric Acid → HCID 20065983, compound

HRID 359059Notes

Reaction equation

HRID 359059 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:37])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18](CC2C=CC=CC=2)[CH2:19][CH:20]([OH:29])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:12][CH:11]=1.Cl>CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:37])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][CH:20]([OH:29])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53782802HCID 53782802, compound

Product 1

HCID 20065983HCID 20065983, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-3- Methoxypropyl 4-[2-(N-benzyl-N-(2-hydroxy-3-phenoxypropyl)amino)ethyl]phenoxyacetamide (2.7g) was dissolved in methanol (130 ml) and acidified to pH3 with an ethereal solution of hydrogen chloride. 10% Palladium on carbon (440 mg) was added and the mixture stirred under an atmosphere of hydrogen for 4 hours. The mixture was filtered through diatomaceous earth and the filtrate evaporated to give a crude product, which was purified by chromatography on K60 silica (55 g) using 10% methanol in dichloromethane as eluant. The product was dissolved in dichloromethane and ethereal hydrogen chloride added to give a pH of 3. The solvent was evaporated and the residue dissolved in dichloromethane which was also evaporated. The residue (1.4 g) was recrystallised from methyl acetate (50 ml) and methanol (15 ml). Thus was obtained N-3- methoxypropyl 4-[2-(2-hydroxy-3-phenoxypropyl-amino)ethyl]phenoxyacetamide (0.75 g), m.p. 167°9°, the NMR data were consistent with those of Example 11.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. customthe filtrate evaporated
  3. customto give a crude product, which
  4. customwas purified by chromatography on K60 silica (55 g)
  5. dissolutionThe product was dissolved in dichloromethane
  6. additionethereal hydrogen chloride added
  7. customto give a pH of 3
  8. customThe solvent was evaporated
  9. dissolutionthe residue dissolved in dichloromethane which
  10. customwas also evaporated
  11. customThe residue (1.4 g) was recrystallised from methyl acetate (50 ml) and methanol (15 ml)

Sources & evidence

ORD record
ord-e5fb8ef20a634e7b8aa41cb9d01e28c2
Source dataset
uspto-grants-1991_03
Patent number
US04999377

Reaction notes

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