Formaldehyde → HCID 18998700, compound

HRID 885430Notes

Reaction equation

HRID 885430 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:29]=[CH:28][C:18]3[NH:19][C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[CH2:22][CH2:23][C:17]=3[CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[C-:30]#[N:31].[K+].[CH2:33]=O.[OH-].[Na+]>C(O)(=O)C.ClCCl>[C:30]([CH2:33][N:19]1[C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[CH2:22][CH2:23][C:17]2[CH:16]=[C:15]([CH2:14][N:13]3[C:6]4=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]4[N:4]=[C:3]3[CH2:1][CH3:2])[CH:29]=[CH:28][C:18]1=2)#[N:31]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 199708722-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepine

Product 1

HCID 18998700HCID 18998700, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

[step 2] 2-(2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepine (55.4 g, 145 mmol) obtained in step 1 was dissolved in acetic acid (500 mL) and the solution was added with potassium cyanide (11 g, 169 mmol) and paraformaldehyde (4.6 g, 152 mmol) at 10° C., followed by stirring at room temperature for 24 hr. The mixture was added to a mixed solution of 10 mol/L aqueous sodium hydroxide solution (900 mL), ice (1 L) and dichloromethane (1 L). The organic layer was washed with 0.1 mol/L aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate/triethylamine=10/10/1) to give 5-cyanomethyl-2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepine (39.0 g, 64%).

Workup

  1. washThe organic layer was washed with 0.1 mol/L aqueous sodium hydroxide solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate/triethylamine=10/10/1)

Sources & evidence

ORD record
ord-b891e32051c44353b53a080a07e9c40e
Source dataset
uspto-grants-2012_08
Patent number
US08242151B2

Reaction notes

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