Dimethylamine → HCID 21286361, compound

HRID 2231197Notes

Reaction equation

HRID 2231197 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[CH3:6][O:7][C:8]1[CH:25]=[CH:24][CH:23]=[CH:22][C:9]=1[CH2:10][O:11][C:12]1[C:13]2[N:14]([CH:18]=[C:19]([CH3:21])[N:20]=2)[CH:15]=[CH:16][CH:17]=1>C(O)(=O)C>[CH3:3][N:4]([CH2:1][C:18]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:9]3[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=3[O:7][CH3:6])[C:13]2=[N:20][C:19]=1[CH3:21])[CH3:5]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 21286352HCID 21286352, compound

Product 1

HCID 21286361HCID 21286361, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 37% aqueous formaldehyde (1.57 g) in acetic acid (25 ml) was added dropwise 50% aqueous dimethylamine (1.75 g) with ice-cooling over a period of 10 minutes and the mixture was stirred for an additional 10 minutes. The mixture was heated at 50°-55° C. for 2 hours after an addition of 8-(2-methoxybenzyloxy)-2-methylimidazo[1,2-a]pyridine (4.96 g) thereto and then evaporated in vacuo. The residue was basified with aqueous sodium hydroxide and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residual solid was recrystallized from diethyl ether to give 3-dimethylaminomethyl-8-(2-methoxybenzyloxy)-2-methylimidazo[1,2-a]pyridine (3.55 g).

Workup

  1. temperaturecooling over a period of 10 minutes
  2. temperatureThe mixture was heated at 50°-55° C. for 2 hours
  3. customevaporated in vacuo
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residual solid was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-d17b9785155042bfbb5cd62ecd64f8b6
Source dataset
uspto-grants-1988_11
Patent number
US04782055

Reaction notes

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