Toluene → HCID 53634043, compound

HRID 1274112Notes

Reaction equation

HRID 1274112 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:12])[O:9][CH2:10][CH3:11].[C:13]([O-:16])([O-])=O.[Na+].[Na+].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.[I-].[K+]>[CH2:8]1[C:25]2[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:16][C:13]=2[CH2:5][CH2:6][N:7]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:12])[O:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 235137HCID 235137, compound

Product 1

HCID 53634043HCID 53634043, compound

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Procedure

A mixture of intermediate (1) (0.03 mol), ethyl (5-chloropentyl)carbamate (0.04 mol), potassium iodide (0.1 g) and Na2CO3 (5.7 g) in toluene (250 ml) was stirred and refluxed overnight. The reaction mixture was cooled, stirred in water (200 ml), and the layers were separated. The organic phase was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 7 g of ethyl [5-(3,4-dihydrobenzofuro[3,2-c]pyridin-2(1H)-yl)pentyl]carbamate (interm. 15).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. customthe layers were separated
  4. customThe organic phase was evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-902a42810148474d876072a7e94a6673
Source dataset
uspto-grants-2000_12
Patent number
US06156757

Reaction notes

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