HCID 54563507, compound → HCID 14739906, compound

HRID 728835Notes

Reaction equation

HRID 728835 reaction equation
[N:1]1([C:6]2[CH:37]=[CH:36][C:9]([O:10][CH2:11][CH2:12][N:13](CC3C=CC=CC=3)[CH2:14][CH:15]([OH:28])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][O:26][CH3:27])=[CH:20][CH:19]=3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>Cl>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][NH:13][CH2:14][CH:15]([OH:28])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][O:26][CH3:27])=[CH:20][CH:19]=3)=[CH:36][CH:37]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

3

Reactant 1

HCID 54563507HCID 54563507, compound

Product 1

HCID 14739906HCID 14739906, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dissolve 6.36 g (.013 mol) 1-[[2-[4-(1H-imidazol-1-yl)phenoxy]ethyl](phenylmethyl)amino]-3-[4-(2-methoxyethyl)phenoxy]-2-propanol in 50 mL 5 M methanolic HCl and remove the solvents in vacuo. Dissolve the residue in glacial acetic acid with 0.86 g10% palladium hydroxide on carbon. The reaction mixture is hydrogenated under 52 psi H2 on a Parr Hydrogenator. Follow the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonia,9:1). At the completion of the reaction, the catalyst is filtered and the solvents are removed in vacuo. The resulting oil is chromatographed on alumina (activity III) using 2% methanol in methylene chloride to provide the title compound.

Workup

  1. customremove the solvents in vacuo
  2. dissolutionDissolve the residue in glacial acetic acid with 0.86 g10% palladium hydroxide on carbon
  3. customthe progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonia,9:1)
  4. customAt the completion of the reaction
  5. filtrationthe catalyst is filtered
  6. customthe solvents are removed in vacuo
  7. customThe resulting oil is chromatographed on alumina (activity III)

Sources & evidence

ORD record
ord-757f059b791243d6aa07ddc3f7e17afc
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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