Dimethylamine → HCID 19013490, compound

HRID 1729107Notes

Reaction equation

HRID 1729107 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]=O.[CH:6]1[N:7]=[CH:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12.[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:2]([CH2:4][C:8]1[N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[CH:6][N:7]=1)[CH3:3]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 274090Imidazo(1,5-a)pyridine

Product 1

HCID 19013490HCID 19013490, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 40% aqueous dimethylamine (10.2 g), formalin (7.4 g), and glacial acetic acid, cooled to 0° to 5° C., was given to imidazo[1,5-a]pyridine [J. Chem. Soc., 1955, 2834](10.0 g, 84 mmol). The resulting dark mixture was left stirring for 48 hours at room temperature,then was made basic with 2N NaOH and extracted with CH2Cl2. The combined extracts (2×100 mL) were dried (Na2SO4) and evaporated. The residue was purified by chromatography over silica gel using MeOH/CH2Cl2 2:98 as eluant to give the title compound (3.0 g, 20%) as an oil; MS (70 eV): m/z 175 (M+).

Workup

  1. temperaturecooled to 0° to 5° C.
  2. waitThe resulting dark mixture was left
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts (2×100 mL) were dried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-90af7fe85d3a432fa0c844fe7225bd7a
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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