Acetic Acid → HCID 22727300, compound

HRID 2086275Notes

Reaction equation

HRID 2086275 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][C:10](=[N:13][N:14]3[CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH:29]=[CH2:30])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH2:16][C:15]3=[O:31])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][N:14]3[CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:24]=[CH:25][C:26]([CH:29]=[CH2:30])=[CH:27][CH:28]=4)(=[O:22])=[O:21])[CH2:16][C:15]3=[O:31])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 69545943HCID 69545943, compound

Product 1

HCID 22727300HCID 22727300, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(4-Pyridyl)-4-piperidinylideneamino]-4-(4-vinylphenylsulfonyl)-2-piperazinone (200 mg) was dissolved in methanol (10 ml), combined with acetic acid (110 mg) with cooling on ice followed by sodium cyanoborohydride (57 mg), and stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue was dissolved in dichloromethane, washed with aqueous sodium bicarbonate and brine, dried, concentrated and purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) to obtain the title compound (150 mg) as a colorless amorphous material.

Workup

  1. temperaturewith cooling on ice
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with aqueous sodium bicarbonate and brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)

Sources & evidence

ORD record
ord-20d8201d7399401197ab1f9248c0a5fb
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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