Benzaldehyde → HCID 19734538, compound

HRID 1588536Notes

Reaction equation

HRID 1588536 reaction equation
[C:1]([NH:3][C:4]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[N:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)#[N:2].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([BH3-])#N.[Na+]>CO>[C:1]([NH:3][C:4]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[N:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][CH:13]=1)#[N:2]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19734488HCID 19734488, compound

Product 1

HCID 19734538HCID 19734538, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-cyano-N'-[2-(4-aminophenyl)ethyl]-3-pyridinecarboximidamide (0.20 g, 0.75 mmol) was dissolved in methanol (15 ml), and benzaldehyde (0.12 g, 1.13 mmol) and sodium cyanoborohydride (0.10 g, 1.59 mmol) were added. The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residue thus obtained was extracted with chloroform (50 ml×3). The chloroform layer was washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual concentrate was subjected to chromatography on a silica gel column (WAKO GEL C-200, 50 g) eluting with chloroform-methanol (100:1). The eluted fractions were concentrated under reduced pressure and crystallized from methanol-diethyl ether to give the title compound (0.12 g, 0.34 mmol, yield: 75%) as colorless needles.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customThe residue thus obtained
  3. extractionwas extracted with chloroform (50 ml×3)
  4. washThe chloroform layer was washed with water (100 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe residual concentrate
  8. washeluting with chloroform-methanol (100:1)
  9. concentrationThe eluted fractions were concentrated under reduced pressure
  10. customcrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-081a216b60d24af590d2bf449adfac86
Source dataset
uspto-grants-1993_06
Patent number
US05223508

Reaction notes

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