Potassium Carbonate → N-((1,3-dioxolan-2-yl)methyl)-3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

HRID 1987919Notes

Reaction equation

HRID 1987919 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH:9]1[O:13][CH2:12][CH2:11][O:10]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH2:30])[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>CS(C)=O>[O:10]1[CH2:11][CH2:12][O:13][CH:9]1[CH2:8][NH:30][C:18]1[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)=[C:16]([O:15][CH3:14])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 117365033-Methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

Product 1

HCID 67214560N-((1,3-dioxolan-2-yl)methyl)-3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of K2CO3 (235 mg, 1.70 mmol), 2-(bromomethyl)-1,3-dioxolane (400 mg, 1.70 mmol), and 3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)benzenamine (3.0 g, 14.5 mmol), preparation described in Patent: WO2002/101146, in DMSO (17 mL) was heated at 80° C. for 24 hr. After removal of any precipitate by filtration, the filtrate was partitioned between EtOAc/H2O (100/20 mL). The organic layer was washed with brine and dried over MgSO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 0%-20% gradient EtOAc/Hexanes to elute the title compound as a yellow brownish oil (150 mg, 27%) MS (ESI) 323 (M+H)+.

Workup

  1. customAfter removal of any precipitate
  2. filtrationby filtration
  3. customthe filtrate was partitioned between EtOAc/H2O (100/20 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent under vacuum
  7. customthe residue was chromatographed on silica gel using 0%-20% gradient EtOAc/Hexanes
  8. washto elute the title compound as a yellow brownish oil (150 mg, 27%)

Sources & evidence

ORD record
ord-0f8f38e2d88b42b18cf085ba000fdecc
Source dataset
uspto-grants-2009_06
Patent number
US07553836B2

Reaction notes

Loading…