Hydrochloric Acid → HCID 9954184, compound

HRID 2108045Notes

Reaction equation

HRID 2108045 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:11][N:12](CC2C=CC=CC=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[OH:10])=[CH:4][C:3]=1[Cl:35].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][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[OH:10])=[CH:4][C:3]=1[Cl:35]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 230450824-Amino-3,5-dichloro-alpha-[[(phenylmethyl)[6-[2-(2-pyridinyl)ethoxy]hexyl]amino]methyl]benzenemethanol

Product 1

HCID 9954184HCID 9954184, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

4-Amino-3,5-dichloro-α-[[(phenylmethyl)[6-[2-(2-pyridinyl)ethoxy]hexyl]amino]methyl]benzenemethanol (1.1 g) was hydrogenated over pre-reduced 10% palladium oxide on carbon (50% aqueous paste, 200 mg) in ethanol (10 ml) containing hydrochloric acid (conc. HCl/ethanol, 1:9 v/v, 4 ml). The catalyst was removed by filtration through hyflo, the solvent was evaporated and the residual oil was partitioned between 8% sodium bicarbonate (25 ml) and ethyl acetate (25 ml). The organic layer was washed with 8% sodium bicarbonate, water and brine, dried and concentrated to an orange oil which was purified by FCC eluting with System C (95:5:1→90:10:1) to give a yellow oil which was triturated with ether-hexane to give the title compound as a white solid (280 mg) m.p. 94°-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 (25 ml) and ethyl acetate (25 ml)
  4. washThe organic layer was washed with 8% sodium bicarbonate, water and brine
  5. customdried
  6. concentrationconcentrated to an orange oil which
  7. customwas purified by FCC
  8. washeluting with System C (95:5:1→90:10:1)
  9. customto give a yellow oil which
  10. customwas triturated with ether-hexane

Sources & evidence

ORD record
ord-ce1458f5b4a24c248515b8d51fdd2a05
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

Loading…