Acetic Acid → HCID 9980864, compound

HRID 623163Notes

Reaction equation

HRID 623163 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([CH2:9][CH2:10][C:11](=O)[CH3:12])[CH:8]=1.[CH2:22]([NH2:34])[CH2:23][C:24]1[CH:33]=[CH:32][C:29]([O:30][CH3:31])=[C:26]([O:27][CH3:28])[CH:25]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH3:28][O:27][C:26]1[CH:25]=[C:24]([CH2:23][CH2:22][NH:34][CH:11]([CH3:12])[CH2:10][CH2:9][C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:33]=[CH:32][C:29]=1[O:30][CH3:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8421HomoveratrylamineHCID 5003444Sodium cyanoborohydrideHCID 140254764-[5-Methoxy-2-(phenylethynyl)phenyl]butan-2-one2×

Product 1

HCID 9980864HCID 9980864, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[5-Methoxy-2-(phenylethynyl)phenyl]-2-butanone (0.5 g, 1.8 mmole), the product of Example 1d, and homoveratryl amine (0.33 g 1.8 mmole) were combined in 10 mL of absolute methanol. With stirring, sodium cyanoborohydride (0.21 g, 3.3 mmole) was added in three portions. During this addition, the pH was adjusted to 6 with glacial acetic acid. After stirring for 5 hr, the reaction mixture was concentrated in vacuo and the resulting residue dissolved in methylene chloride. The methylene chloride solution was washed with 1N sodium hydroxide, water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 0.72 g of the title compound as a golden oil. The free base was dissolved in absolute methanol (5 mL) and treated with oxalic acid (0.2 g). After stirring for several hours, ether (50 mL) was added and the solution was cooled and filtered to give 1.0 g of the title compound as the oxalate salt.

Workup

  1. additionDuring this addition
  2. stirringAfter stirring for 5 hr
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutionthe resulting residue dissolved in methylene chloride
  5. washThe methylene chloride solution was washed with 1N sodium hydroxide, water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae564e21c596480889a0b9ba03431260
Source dataset
uspto-grants-1988_09
Patent number
US04772755

Reaction notes

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