Hydrochloric Acid → HCID 19101834, compound

HRID 2372568Notes

Reaction equation

HRID 2372568 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:11][N:12]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]#[C:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:40][CH3:41])[CH:36]=3)[CH:31]=2)CC2C=CC=CC=2)[OH:10])=[CH:4][C:3]=1[Cl:42].Cl>C(O)C.[Pd]>[NH2:1][C:2]1[C:3]([Cl:42])=[CH:4][C:5]([CH:9]([CH2:11][NH:12][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:40][CH3:41])[CH:36]=3)[CH:31]=2)[OH:10])=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19101824HCID 19101824, compound

Product 1

HCID 19101834HCID 19101834, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 4-amino-3,5-dichloro-α-[[[6-[[3-[6-methoxy-2-naphthalenyl]-2-propynyl]oxy]hexyl](phenylmethyl)amino]methyl]benzenemethanol (1.11 g) in absolute ethanol (50 ml) was hydrogenated over pre-reduced 10% palladium on charcoal catalyst (0.4 g) in absolute ethanol (10 ml) containing hydrochloric acid (1:9 conc. hydrochloric acid/ethanol, 1.67 ml). The mixture was filtered through hyflo and evaporated in vacuo to give an oil. The oil was partitioned between dichloromethane (150 ml) and 8% sodium bicarbonate (100 ml). The aqueous phase was re-extracted with dichloromethane (100 ml) and the combined organic extracts dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System C (95:5:1) gave the title compound as a white solid (513 mg), m.p. 102.5°-103.5°.

Workup

  1. filtrationThe mixture was filtered through hyflo
  2. customevaporated in vacuo
  3. customto give an oil
  4. customThe oil was partitioned between dichloromethane (150 ml) and 8% sodium bicarbonate (100 ml)
  5. extractionThe aqueous phase was re-extracted with dichloromethane (100 ml)
  6. customthe combined organic extracts dried
  7. customevaporated in vacuo
  8. customto give an oil
  9. customPurification by FCC
  10. washeluting with System C (95:5:1)

Sources & evidence

ORD record
ord-be6c22ef5b234029ab18a4693483fed6
Source dataset
uspto-grants-1992_03
Patent number
US05099068

Reaction notes

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