1-Iodopentane → HCID 15057257, compound

HRID 1085429Notes

Reaction equation

HRID 1085429 reaction equation
[O:1]=[C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[NH:3]1.[H-].[Na+].I[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>O1CCCC1.ClCCl>[O:1]=[C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]1[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 123351-Iodopentane2×HCID 24758Sodium hydride2×HCID 76175RO-05-2921

Product 1

HCID 15057257HCID 15057257, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 g of 2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine were dissolved in 100 ml of tetrahydrofuran under a nitrogen atmosphere. 1.4 g of sodium hydride in the form of an 80% oily suspension were added in portions to the solution under the nitrogen atmosphere, and the reaction mixture was heated to reflux for 30 minutes. 9.2 g (=5.5 ml) of iodopentane were slowly added dropwise, the mixture was heated to reflux for a further 1.5 hours and then another 0.3 g of sodium hydride in the form of an oily suspension was added and, after a further 10 minutes, another 5.5 ml of iodopentane were added dropwise, and the mixture was heated to reflux for a further hour. To work up the reaction mixture, ice-water was added to the reaction mixture and it was diluted with dichloromethane, the aqueous phase was separated, and the organic phase was washed to neutrality with water, dried over sodium sulfate, filtered and evaporated. 13.5 g of crude product were obtained and were purified by flash chromatography on about 300 g of silica gel using cyclohexane/ethyl acetate 1:1 as the eluent. The purified product was crystallized from cyclohexane and dried. 6.2 g of pure 2-oxo-1-n-pentyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine having a melting point of 93-95° C. were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture was heated
  4. temperatureto reflux for a further 1.5 hours
  5. temperaturethe mixture was heated
  6. temperatureto reflux for a further hour
  7. additionwas added to the reaction mixture and it
  8. customthe aqueous phase was separated
  9. washthe organic phase was washed
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. custom13.5 g of crude product were obtained
  14. customwere purified by flash chromatography on about 300 g of silica gel
  15. customThe purified product was crystallized from cyclohexane
  16. customdried

Sources & evidence

ORD record
ord-cdc3efe3c7cd44ee9e99913b8a993321
Source dataset
uspto-grants-1991_04
Patent number
US05010076

Reaction notes

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