Potassium Carbonate → HCID 14835241, compound

HRID 1084906Notes

Reaction equation

HRID 1084906 reaction equation
Cl.[CH3:2][NH:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH2:5]1.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([CH2:23][CH2:24]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:2][N:3]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH2:5]1)[CH2:24][CH2:23][C:22]1[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 14835238HCID 14835238, compound

Product 1

HCID 14835241HCID 14835241, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methylamino-5-nitroindane hydrochloride (0.45 g), 4-nitrophenethyl bromide (0.46 g) and potassium carbonate (2 g) were heated under reflux in acetonitrile (30 ml) for 3 days. The reaction mixture was then filtered, the filtrate evaporated in vacuo, and the residue purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 1%). The product-containing fractions were combined and evaporated in vacuo to give a gum which was crystallised from ethanol affording the title compound, yield 0.16 g, m.p. 138°-141°.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customthe filtrate evaporated in vacuo
  3. customthe residue purified by column chromatography on silica eluting with methylene chloride
  4. additioncontaining methanol (0% up to 1%)
  5. customevaporated in vacuo
  6. customto give a gum which
  7. customwas crystallised from ethanol affording the title compound, yield 0.16 g, m.p. 138°-141°

Sources & evidence

ORD record
ord-fd54f23327a84e499045a714d477ce48
Source dataset
uspto-grants-1991_04
Patent number
US05006561

Reaction notes

Loading…