Potassium Carbonate → HCID 86750386, compound

HRID 1451654Notes

Reaction equation

HRID 1451654 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:27][NH:28][CH3:29])[CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:26][O:25][C:21]1[CH:20]=[C:19]([CH2:27][N:28]([CH3:29])[CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[CH:18]=[C:17]([O:16][CH3:15])[C:22]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 521855N-METHYL-3,4,5-TRIMETHOXYBENZYLAMINEHCID 118446171-(3-Chloropropoxy)-4-nitrobenzene

Product 1

HCID 86750386HCID 86750386, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3-chloropropoxy)-4-nitrobenzene (4.6 g), 3,4,5-trimethoxy-N-methylbenzenemethanamine (4.1 g; Sigma) and potassium carbonate (2.9 g) in DMF (60 ml) was heated at 70° for 24 h. The mixture was then filtered and the filtrate evaporated. The residue was taken up in water and extracted with dichloromethane. The organic layer was washed with water, dried, evaporated and purified by column chromatography eluting with dichloromethane/methanol (99:1) to give the title compound (5.8 g) as a yellow oil. NMR includes signals at d 2.15 (3H,s,N-CH3), 3.3 (2H,s,CH2 --Ar), 3.7 (9H,s,OCH3).

Workup

  1. temperaturewas heated at 70° for 24 h
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. customdried
  7. customevaporated
  8. custompurified by column chromatography
  9. washeluting with dichloromethane/methanol (99:1)

Sources & evidence

ORD record
ord-9198dd8cef6042e9b006b43c75390ad0
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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