Dimethylamine → HCID 12074949, compound

HRID 647501Notes

Reaction equation

HRID 647501 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CNC>O>[NH2:16][CH2:15][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 132175412-{[3-(Benzyloxy)pyridin-2-yl]methyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 12074949HCID 12074949, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Heat 75 gm of 3-benzyloxy-2-phthalimidomethylpyridine under reflux for one hour in 550 ml of a 40% aqueous dimethylamine solution. Cool the resulting reaction mixture to room temperature, then dilute it with 550 ml water and extract with dichloromethane. Wash the dichloromethane extract with brine and dry over anhydrous sodium sulfate. Filter the dried reaction mixture and remove the solvent dichloromethane from the filtrate under reduced pressure, yielding 2-aminomethyl-3-phenylmethoxypyridine, BP 145°-155°/0.5 mm.

Workup

  1. temperatureCool
  2. customthe resulting reaction mixture to room temperature
  3. extractionextract with dichloromethane
  4. washWash the dichloromethane
  5. extractionextract with brine
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationFilter
  8. customthe dried reaction mixture
  9. customremove the solvent dichloromethane from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-6fa904c302dd48f986b7419cefb74d14
Source dataset
uspto-grants-1983_10
Patent number
US04409226

Reaction notes

Loading…