Sodium hydride → N-ethoxycarbonylpentyl-N-phenylamine

HRID 1457603Notes

Reaction equation

HRID 1457603 reaction equation
[H-].[Na+].C(O[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.BrC[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O>[CH2:29]([O:28][C:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:11][NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 319368Benzyl phenylcarbamate

Product 1

HCID 22099392N-ethoxycarbonylpentyl-N-phenylamineYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under ice-cooling, 1.87 g of 62% sodium hydride was added to 100 ml of a dimethylformamide (DMF) solution containing 10.00 g of N-benzyloxycarbonylaniline, and the mixture was stirred at room temperature for one hour. Under ice-cooling, to the above mixture was added dropwise 50 ml of a DMF solution containing 10.31 g of ethyl 6-bromohexanoate, and the resulting mixture was stirred at room temperature overnight. DMF was removed under reduced pressure and water was added to the residue. The mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was dissolved in 160 ml of methanol and 2 g of 10% palladium-carbon (Pd-C) was added to the solution. The mixture was subjected to catalytic reduction at normal temperature under normal pressure for 2 hours. After removing the catalyst by filtration, the filtrate was condensed and the residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) to give 8.13 g of N-ethoxycarbonylpentyl-N-phenylamine (yield; 79%, melting point: 34°-37° C.).

Workup

  1. temperatureUnder ice-cooling
  2. temperatureUnder ice-cooling, to the above mixture
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. customDMF was removed under reduced pressure and water
  5. additionwas added to the residue
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe extract was washed
  8. customdried
  9. customthe solvent was removed under reduced pressure
  10. dissolutionThe residue was dissolved in 160 ml of methanol
  11. addition2 g of 10% palladium-carbon (Pd-C) was added to the solution
  12. waitThe mixture was subjected to catalytic reduction at normal temperature under normal pressure for 2 hours
  13. customAfter removing the catalyst
  14. filtrationby filtration
  15. customcondensed
  16. customthe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-ceb1099c0ee7463fb5a0922e6296dd08
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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