HCID 24824075, compound → HCID 24824076, compound

HRID 1866186Notes

Reaction equation

HRID 1866186 reaction equation
C([N:8]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27](O)[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[OH:11])C1C=CC=CC=1>Cl.O1CCOCC1>[Cl:18][C:14]1[CH:13]=[C:12]([C@@H:10]([OH:11])[CH2:9][NH:8][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=3)=[CH:25][CH:26]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 24824075HCID 24824075, compound

Product 1

HCID 24824076HCID 24824076, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-[[4-[2-[N-benzyl-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl](hydroxy)-methyl]phenol (545 mg) in 4N hydrogen chloride in 1,4-dioxane (1.0 ml) was stirred for 5 minutes. The solvent was removed by evaporation. A suspension of the residue in ethanol (2.2 ml) and chlorobenzene (5.2 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 55 mg) under hydrogen atmosphere for 2 hours. The catalyst was filtered off, and the filtrate was evaporated. The residue was diluted with ethyl acetate and saturated sodium biscarbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 4-[4-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]benzyl]phenol (395 mg).

Workup

  1. customThe solvent was removed by evaporation
  2. additionA suspension of the residue in ethanol (2.2 ml)
  3. waitchlorobenzene (5.2 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 55 mg) under hydrogen atmosphere for 2 hours
  4. filtrationThe catalyst was filtered off
  5. customthe filtrate was evaporated
  6. additionThe residue was diluted with ethyl acetate and saturated sodium biscarbonate solution
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d367d7ad6942494a8f609d275aeee53e
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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