Water → HCID 12909394, compound

HRID 2397873Notes

Reaction equation

HRID 2397873 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16](Br)[CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1.[CH3:24][N:25](C)C=O.O.[C-]#N.[Na+]>C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([C:24]#[N:25])[CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]2=3)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 12909393HCID 12909393, compound

Product 1

HCID 12909394HCID 12909394, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent2×

Procedure

A mixture of 9.17 gm. (0.0249 mol) of 1-methyl-4-(3-bromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, 4.58 gm. (0.0498 mol) of cuprous cyanide, and 30 ml. of dry dimethylformamide is stirred and heated under reflux for 6.5 hr. To the cooled solution (25° C.) is added 54 ml. of water, 27 ml. of a saturated aqueous solution of sodium cyanide, and 75 ml. of benzene. The mixture is stirred until a two phase system is obtained. The benzene phase is removed and the aqueous phase is extracted with two 75 ml. portions of benzene. The combined benzene phases are washed with 100 ml. of aqueous 0.1M sodium cyanide, three 100 ml. portions of water, and dried over magnesium sulfate. After filtering, evaporation of the benzene gives 7.40 gm. of a crystalline residue. This material is dissolved in the minimum volume of chloroform and passed over an alumina column (15" × 1-) packed in chloroform. The column is eluted with chloroform. Evaporation of the chloroform gives a crystalline product that is recrystallized from isopropyl alcohol to give pure 1-methyl-4-(3-cyano-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, m.p. 152°-154° C.

Workup

  1. additionA mixture of 9.17 gm
  2. temperatureheated
  3. temperatureunder reflux for 6.5 hr
  4. additionTo the cooled solution (25° C.) is added 54 ml
  5. customis obtained
  6. customThe benzene phase is removed
  7. extractionthe aqueous phase is extracted with two 75 ml
  8. washThe combined benzene phases are washed with 100 ml
  9. dry with materialportions of water, and dried over magnesium sulfate
  10. filtrationAfter filtering
  11. customevaporation of the benzene
  12. customgives 7.40 gm
  13. washThe column is eluted with chloroform
  14. customEvaporation of the chloroform
  15. customgives a crystalline product that
  16. customis recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-ea72783e6f0f4aa9a418befe6d5601f0
Source dataset
uspto-grants-1977_05
Patent number
US04022902

Reaction notes

Loading…