Cyclobenzaprine → 5H-Dibenzo(a,d)cycloheptene

HRID 2071722Notes

Reaction equation

HRID 2071722 reaction equation
CN(C)CCC=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2.N#CBr>C1C=CC=CC=1>[CH:17]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:6][C:7]=2[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 2895CyclobenzaprineHCID 10476Cyanogen Bromide

Product 1

HCID 674925H-Dibenzo(a,d)cycloheptene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 23.06 g. (0.0834 mole) of 5-(3-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene in 61 ml. of benzene is added dropwise to a stirred solution of 9.80 g. (0.0917 mole) of cyanogen bromide in 38 ml. of benzene. Some heat is evolved. The mixture is stirred for 3 hours at room temperature, and filtered to remove any precipitate which forms. The filtrate, together with a benzene wash of the precipitate, is evaporated to dryness on a steam-bath under reduced pressure to remove excess cyanogen bromide and solvent. The residual crude cyanamide is dissolved in benzene, and the solution is washed with dilute hydrochloric acid to remove any unchanged amine, then with water. The benzene solution is then evaporated under reduced pressure leaving 5-[3-N-cyano-N-methyl)aminopropylidene]-5H-dibenzo[a,d]cycloheptene as a yellow oil weighing typically 19.6 g.

Workup

  1. filtrationfiltered
  2. customto remove any precipitate which
  3. washThe filtrate, together with a benzene wash of the precipitate
  4. customis evaporated to dryness on a steam-bath under reduced pressure
  5. customto remove excess cyanogen bromide and solvent
  6. dissolutionThe residual crude cyanamide is dissolved in benzene
  7. washthe solution is washed with dilute hydrochloric acid
  8. customto remove any unchanged amine
  9. customThe benzene solution is then evaporated under reduced pressure

Sources & evidence

ORD record
ord-3585f5c409274b759ff9e2902676527c
Source dataset
uspto-grants-1977_09
Patent number
US04048223

Reaction notes

Loading…