Dimethylamine → 8-(2-Chlorobenzyloxy)-3-dimethylaminomethyl-2-methylimidazo[1,2-a]pyridine
Reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[Cl:6][C:7]1[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=1[CH2:9][O:10][C:11]1[C:12]2[N:13]([CH:17]=[C:18]([CH3:20])[N:19]=2)[CH:14]=[CH:15][CH:16]=1>C(O)(=O)C>[Cl:6][C:7]1[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=1[CH2:9][O:10][C:11]1[C:12]2[N:13]([C:17]([CH2:3][N:4]([CH3:1])[CH3:5])=[C:18]([CH3:20])[N:19]=2)[CH:14]=[CH:15][CH:16]=1Participants
Procedure
To a solution of 37% aqueous formaldehyde (2.38 g) in acetic acid (38 ml) was added dropwise 50% aqueous dimethylamine (2.63 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-chlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (7.6 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 a mixture of diethyl ether and n-hexane to give 8-(2-chlorobenzyloxy)-3-dimethylaminomethyl-2-methylimidazo[1,2-a]pyridine (7.85 g).
Workup
- temperaturecooling over a period of 10 minutes
- temperatureThe mixture was heated at 50°-55° C. for 2 hours
- customevaporated in vacuo
- extractionextracted with methylene chloride
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residual solid was recrystallized from a mixture of diethyl ether and n-hexane
Sources & evidence
- ORD record
- ord-92e60f8984b44a1db9d8ae0442b210af
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04725601
Reaction notes
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