Formaldehyde → HCID 86667174, compound

HRID 528772Notes

Reaction equation

HRID 528772 reaction equation
[Cl:1][C:2]1[N:3]2[C:7]([N:8]=[C:9]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:10]=13)=[CH:6][CH:5]=[N:4]2.C=O.[C:18](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C([O-])([O-])=O.[K+].[K+]>[Cl:1][C:2]1[N:3]2[C:7]([N:8]=[C:9]3[CH2:15][CH2:14][N:13]([CH3:18])[CH2:12][CH2:11][C:10]=13)=[CH:6][CH:5]=[N:4]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 71741720HCID 71741720, compound

Product 1

HCID 86667174HCID 86667174, compound

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

To 20.0 g (77.2 mmol) 10-Chloro-6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]indene in 200 mL buffer (pH=5) 6.4 mL formaldehyde (37% in water, 84.9 mmol) and 19.7 g sodium triacetoxyborohydride (93.0 mmol) were added under cooling with ice and stirring was continued over night. The mixture was then diluted at 0° C. with K2CO3-solution (15% in water) and extracted with ethyl acetate. The organic layers were combined, dried (Na2SO4) and concentrated. The residue was then purified by column chromatography (silica, EtOAc/MeOH/NH4OH=9:1:0.1) to give the desired product.

Workup

  1. temperatureunder cooling with ice
  2. waitwas continued over night
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was then purified by column chromatography (silica, EtOAc/MeOH/NH4OH=9:1:0.1)

Sources & evidence

ORD record
ord-72841c81baff4ba9b9fea322e48842c6
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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