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Dimethylformamide → N-[3-(6-Dimethylaminomethyl-2-pyridyloxy)propyl]formamide

HRID 1154703
Notes
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Reaction equation

HRID 1154703 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 90863-Amino-1-propanolHCID 24758Sodium hydrideHCID 20434272[(6-Chloropyridin-2-yl)methyl]dimethylamine

Product 1

HCID 20434286N-[3-(6-Dimethylaminomethyl-2-pyridyloxy)propyl]formamide

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

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

  1. temperatureThe reaction temperature is increased to 125° C. for 3 hours
  2. temperatureThen the reaction is cooled
  3. filtrationthe precipitated salts filtered
  4. customThe solvents are removed under vacuum
  5. dissolutionThe residue is dissolved in chloroform
  6. washwashed with water
  7. extractionextracted into dilute hydrochloric acid
  8. extractionthe acidic extract
  9. extractionThe crude product is extracted into chloroform
  10. customdried
  11. customevaporated (7.6 g)
  12. washeluting with 3-8% methanol/chloroform

Sources & evidence

ORD record
ord-2c2a6c194aad4faab5c112958f1e055d
Source dataset
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04490533

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes