Hydrochloric Acid → HCID 14210576, compound

HRID 2108047Notes

Reaction equation

HRID 2108047 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][CH2:28][CH2:29][CH2:30][C:31]2[C:36]([OH:37])=[CH:35][CH:34]=[CH:33][N:32]=2)CC2C=CC=CC=2)[OH:10])=[CH:4][C:3]=1[Cl:38].Cl>C(O)C.[Pd]=O>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][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][CH2:30][C:31]2[C:36]([OH:37])=[CH:35][CH:34]=[CH:33][N:32]=2)[OH:10])=[CH:4][C:3]=1[Cl:38]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23045069HCID 23045069, compound

Product 1

HCID 14210576HCID 14210576, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

4-Amino-3,5-dichloro-α-[[[6-[4-(3-hydroxy-2-pyridinyl)butoxy]hexyl](phenylmethyl)amino]methyl]benzenemethanol (0.49 g) was hydrogenated over pre-reduced 10% palladium oxide on carbon (50% aqueous paste, 100 mg) in ethanol (10 ml) containing hydrochloric acid (conc. HCl/ethanol, 1:9 v/v, 1.6 ml). The catalyst was removed by filtration through hyflo, the solvent was evaporated and the residual oil was partitioned between 8% sodium bicarbonate (15 ml) and ethyl acetate (15 ml). The organic layer was washed with 8% sodium bicarbonate (10 ml), water (10 ml) and brine (10 ml), dried and concentrated to a yellow oil which was purified by FCC eluting with System C (95:5:1) to give a pale yellow oil which was triturated with ether to give the title compound as a white solid (215 mg) m.p. 95°-96°.

Workup

  1. customThe catalyst was removed by filtration through hyflo
  2. customthe solvent was evaporated
  3. customthe residual oil was partitioned between 8% sodium bicarbonate (15 ml) and ethyl acetate (15 ml)
  4. washThe organic layer was washed with 8% sodium bicarbonate (10 ml), water (10 ml) and brine (10 ml)
  5. customdried
  6. concentrationconcentrated to a yellow oil which
  7. customwas purified by FCC
  8. washeluting with System C (95:5:1)
  9. customto give a pale yellow oil which
  10. customwas triturated with ether

Sources & evidence

ORD record
ord-89e7a197b132459a8d23278ed143534a
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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