Dimethylformamide → N-[3-(6-Dimethylaminomethyl-2-pyridyloxy)propyl]formamide
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[CH3:8][N:9]([CH2:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][CH:13]=1)[CH3:10].CN(C)[CH:21]=[O:22]>C(O)C>[CH3:8][N:9]([CH2:11][C:12]1[N:17]=[C:16]([O:5][CH2:4][CH2:3][CH2:2][NH:1][CH:21]=[O:22])[CH:15]=[CH:14][CH:13]=1)[CH3:10]Participants
Conditions
- Temperature
- 80 °C
Procedure
3-Aminopropanol (2.55 g, 0.034 mol) is added to a suspension of 60% sodium hydride in mineral oil (1.29 g, 0.033 mol) in dry dimethylformamide (30 ml) and the mixture is warmed to 80° C. before adding dropwise a solution of 6-dimethylaminomethyl-2-chloropyridine (5.45 g, 0.032 mol) in 30 ml of dry dimethylformamide. The reaction temperature is increased to 125° C. for 3 hours. Then the reaction is cooled, diluted with ethanol and the precipitated salts filtered. The solvents are removed under vacuum. The residue is dissolved in chloroform, washed with water, extracted into dilute hydrochloric acid and the acidic extract neutralized with sodium carbonate. The crude product is extracted into chloroform dried and evaporated (7.6 g). This residue is chromatorgrphed on silica gel (200 g) eluting with 3-8% methanol/chloroform to give 3.2 g of pure product as an oil.
Workup
- temperatureThe reaction temperature is increased to 125° C. for 3 hours
- temperatureThen the reaction is cooled
- filtrationthe precipitated salts filtered
- customThe solvents are removed under vacuum
- dissolutionThe residue is dissolved in chloroform
- washwashed with water
- extractionextracted into dilute hydrochloric acid
- extractionthe acidic extract
- extractionThe crude product is extracted into chloroform
- customdried
- customevaporated (7.6 g)
- washeluting with 3-8% methanol/chloroform
Sources & evidence
- ORD record
- ord-2c2a6c194aad4faab5c112958f1e055d
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04490533
Reaction notes
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