HCID 19876751, compound → HCID 19876774, compound

HRID 1886034Notes

Reaction equation

HRID 1886034 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][C:29]2[O:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=2)CC2C=CC=CC=2)[OH:10])=[CH:4][C:3]=1[Cl:38].Cl.C(O)C>C(O)C.[Pd]>[NH2:1][C:2]1[C:3]([Cl:38])=[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][C:29]2[O:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=2)[OH:10])=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 19876751HCID 19876751, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 19876774HCID 19876774, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-amino-3,5-dichloro-α-[[[6-[2-(2-benzoxazolyl)ethoxy]hexyl](phenylmethyl)amino]methyl]benzenemethanol (1.09 g) in ethanol (25 ml) containing conc. hydrochloric acid-ethanol (1:9, 1.78 ml) was added to a pre-hydrogenated suspension of 10% palladium on carbon (50% aqueous paste, 0.65 g) and hydrogenated at room temperature and pressure, then filtered through hyflo and evaporated in vacuo. The residue was partitioned between 8% sodium bicarbonate (25 ml) and ethyl acetate (50 ml) and the organic phase dried and evaporated in vacuo to a semi solid. Purification by FCC over silica (Merck 60) eluting with System B (97:2:1→94:5:1) afforded the title compound as a gum, which crystallised after trituration with hexane to a white solid (613 mg) m.p. 85°-87°.

Workup

  1. filtrationpressure, then filtered through hyflo
  2. customevaporated in vacuo
  3. customThe residue was partitioned between 8% sodium bicarbonate (25 ml) and ethyl acetate (50 ml)
  4. customthe organic phase dried
  5. customevaporated in vacuo to a semi solid
  6. customPurification by FCC over silica (Merck 60)
  7. washeluting with System B (97:2:1→94:5:1)

Sources & evidence

ORD record
ord-b617722357424dcd9bcc194c4f48190f
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

Loading…