Hydrochloric Acid → HCID 12288800, compound

HRID 1167063Notes

Reaction equation

HRID 1167063 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)/[N:8]=[CH:9]\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 178482788HCID 178482788, compound

Product 1

HCID 12288800HCID 12288800, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[di(2-pyridinyl)methyl]-N-[(Z)-2-pyridinylmethylidene]amine (1.5 g, 5.5 mmol) in methanol (20 ml) was added NaBH4 (0.45 g, 11.8 mmol) in small portions. After stirring at room temperature for 2 hours HCl (aq) is added until the pH<2. After stirring for 30 min 5 N NaOH (aq) is added until the pH>9. The methanol is removed through evaporation and the aqueous layer is extracted with ethyl acetate (3×30 ml). The combined ethyl acetate layers are washed with brine (30 ml) and dried (Na2SO4). Evaporation of the solvent gave N-[di(2-pyridinyl)methyl]-N-(2-pyridinylmethyl)amine (N3Py) (1.35 g, 89%) as a yellow oil. 1H-NMR (CDCl3, 300 MHz) δ 3.85 (s, 2H), 5.10 (s, 1H), 7.03 (m, 3H), 7.41 (m, 6H), 8.46 (m, 3H); 13C NMR (CDCl3, 50 MHz) δ 53.1 (t), 68.9 (d), 121.8 (d), 122.1 (d), 122.2 (d), 122.3 (d), 136.3 (d), 136.5 (d), 149.2 (d), 159.6 (s), 161.2 (s); MS (CI): m/z 277 (M+1).

Workup

  1. additionis added until the pH<2
  2. additionis added until the pH>9
  3. customThe methanol is removed through evaporation
  4. extractionthe aqueous layer is extracted with ethyl acetate (3×30 ml)
  5. washThe combined ethyl acetate layers are washed with brine (30 ml)
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-49e6991e978a43ea94ce13444d6321fc
Source dataset
uspto-grants-2003_09
Patent number
US06617299B1

Reaction notes

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