Hydrochloric Acid → HCID 14210571, compound

HRID 2108044Notes

Reaction equation

HRID 2108044 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]/[CH:21]=[CH:22]\[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[OH:10])=[CH:4][C:3]=1[Cl:36].Cl>C(O)C.[Pd]>[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][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[OH:10])=[CH:4][C:3]=1[Cl:36]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70362000HCID 70362000, compound

Product 1

HCID 14210571HCID 14210571, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (Z)-4-amino-3,5-dichloro-α-[[(phenylmethyl)[6-[[3-(2-pyridinyl)-2-propenyl]oxy]hexyl]amino]methyl]benzenemethanol (0.65 g) in ethanol (15 ml) containing hydrochloric acid (2.7 mmol) was hydrogenated over 10% palladium on charcoal (0.15 g), filtered and evaporated. The residue was partitioned between aqueous sodium bicarbonate (1M; 30 ml) and ethyl acetate (150 ml) and the dried organic phase was evaporated to give a brown gum. The gum was purified by FCC eluting with System A (93:7:1→85:15:1), to give the title compound as a white solid (0.32 g) m.p. 38°-41°.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was partitioned between aqueous sodium bicarbonate (1M; 30 ml) and ethyl acetate (150 ml)
  4. customthe dried organic phase was evaporated
  5. customto give a brown gum
  6. customThe gum was purified by FCC
  7. washeluting with System A (93:7:1→85:15:1)

Sources & evidence

ORD record
ord-023d1bfae64f424cb6907addd5e0af8d
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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