Acetic Acid → HCID 68522195, compound

HRID 884081Notes

Reaction equation

HRID 884081 reaction equation
[CH2:1]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:27])[CH2:18][NH:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.C(O)(=O)C.C(O[C:35]1(O[Si](C)(C)C)[CH2:37][CH2:36]1)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:27])[CH2:18][N:19]([CH:35]2[CH2:37][CH2:36]2)[C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)[CH2:13][CH2:12]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 68525824HCID 68525824, compound

Product 1

HCID 68522195HCID 68522195, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(4-piperonylpiperazin-1-yl)-2-(4-hydroxyphenylamino)ethanone (1.00 g, 2.7 mmol) in methanol (10 mL) were added acetic acid (1.55 mL, 27 mmol), molecular sieves 3A1/16 (1.00 g), [(1-ethoxycyclopropyl)oxy]trimethylsilane (0.653 mL, 3.2 mmol) and sodium cyanoborohydride (770 mg, 12 mmol). The resulting solution was stirred for 16 hours at 60° C. This reaction solution was filtered and concentrated, and to the residue were added ethyl acetate and water. The aqueous layer was adjusted to pH 10 using aqueous 6 N sodium hydroxide. This layer was stirred for some time, and once insoluble matter had dissolved, the ethyl acetate layer was removed, and washed with aqueous 2 N sodium hydroxide and a saturated sodium bicarbonate solution, then dried over anhydrous magnesium sulfate. The solvent was evaporated, to thereby yield 770 mg of the title compound.

Workup

  1. filtrationThis reaction solution was filtered
  2. concentrationconcentrated
  3. additionto the residue were added ethyl acetate and water
  4. stirringThis layer was stirred for some time, and once insoluble matter
  5. dissolutionhad dissolved
  6. customthe ethyl acetate layer was removed
  7. washwashed with aqueous 2 N sodium hydroxide
  8. dry with materiala saturated sodium bicarbonate solution, then dried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5ebde4c48a404eefb6c52363b440d57a
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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