HCID 67894945, compound → HCID 14891483, compound

HRID 466365Notes

Reaction equation

HRID 466365 reaction equation
Cl.[CH2:2]([N:4]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=1)=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH3:3].[H][H]>[Pd].CO>[CH2:2]([N:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:23])=[O:24])=[CH:17][CH:16]=1)[OH:14])[CH3:3]

Participants

5

Reactant 2

HCID 67894945HCID 67894945, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14891483HCID 14891483, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-[4-[(ethylheptylamino)acetyl]phenyl]methanesulfonamide monohydrochloride as prepared in Preparation 6 (4.0 g, 0.0103 mol) and 150 ml of MeOH is reduced in a Parr hydrogenator using 10% palladium-on-carbon (0.3 g) at an initial hydrogen pressure of 50 PSI. After 18 hours the reaction mixture is filtered over Celite and the filtrate is concentrated in vacuo. The residue is mixed with NaHCO3 and extracted well with CH2Cl2. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue is then dissolved in Et2O, treated with Darco, and crystallized from Et2O:Pet ether to yield 3.1 g of N-[4-[2-(ethylheptylamino)-1-hydroxyethyl]phenyl]methanesulfonamide, m.p. 65°-67° C. The analytical sample has m.p. 71°-72° C.

Workup

  1. filtrationAfter 18 hours the reaction mixture is filtered over Celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. additionThe residue is mixed with NaHCO3
  4. extractionextracted well with CH2Cl2
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue is then dissolved in Et2O
  9. additiontreated with Darco
  10. customcrystallized from Et2O

Sources & evidence

ORD record
ord-a654567679174472b1e2fe7dd0843622
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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