Sodium hydride → HCID 20535768, compound

HRID 1156284Notes

Reaction equation

HRID 1156284 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[O:6][CH2:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH:10]([C:11]#[N:12])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25]Cl>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[O:6][CH2:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10]([C:11]#[N:12])([CH2:25][CH2:24][CH2:23][N:22]([CH3:27])[CH3:21])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 12962153HCID 12962153, compound

Product 1

HCID 20535768HCID 20535768, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

2-Chloro-11-cyano-6,11-dihydrodibenz[b,e]oxepin (4.6 g; 0.017 mole) of Example 25B is dissolved in dry dimethylformamide (DMF) [40 ml] under nitrogen and cooled to 5° C. Sodium hydride (99%) (0.45 g; 0.018 mole) is added in one portion and stirred for five minutes. It is then brought to ambient temperature and stirred for thirty minutes. After cooling to 3° C. 3-dimethylaminopropyl chloride (2.18 g; 0.018 mole) in dry DMF (20 ml) is added dropwise. Upon completion of the addition, the reaction mixture is brought to ambient temperature for thirty minutes and then heated at 60° C. for eight hours. The reaction mixture is cooled and poured with stirring into 600 ml ice water. The resulting solid is filtered, dissolved in ether and extracted with 2 N HCl. The acidic aqueous portion is basified with 10% NaOH and the precipitate filtered and dried. The solid is dissolved in ether and treated with ethereal HCl. After filtering, the solid is washed with ether and dried. Recrystallization from acetonitrile provides 1.0 g (16%) of crystals of 2-chloro-11-cyano-11-[3(dimethylamino)propyl]-6,11-dihydrodibenz[b,e]oxepin hydrochloride, m.p. 217°-219° C.

Workup

  1. customis then brought to ambient temperature
  2. stirringstirred for thirty minutes
  3. temperatureAfter cooling to 3° C
  4. additionUpon completion of the addition
  5. waitthe reaction mixture is brought to ambient temperature for thirty minutes
  6. temperatureheated at 60° C. for eight hours
  7. temperatureThe reaction mixture is cooled
  8. additionpoured
  9. filtrationThe resulting solid is filtered
  10. dissolutiondissolved in ether
  11. extractionextracted with 2 N HCl
  12. filtrationthe precipitate filtered
  13. customdried
  14. dissolutionThe solid is dissolved in ether
  15. additiontreated with ethereal HCl
  16. filtrationAfter filtering
  17. washthe solid is washed with ether
  18. customdried
  19. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-9feed27d1ee448769773e71e27e24294
Source dataset
uspto-grants-1982_06
Patent number
US04335122

Reaction notes

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