Pyridine → N-[(10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-yl)methyl]-4-pyridinamine

HRID 358383Notes

Reaction equation

HRID 358383 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH:14]1[C:24]2[CH2:23][CH2:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[CH:19]([C:29](Cl)=O)[C:18]=2[CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.O>[CH:14]1[C:24]2[CH2:23][CH2:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[CH:19]([CH2:29][NH:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 17274-AminopyridineHCID 1251564810,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonyl chloride

Product 1

HCID 20448939N-[(10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-yl)methyl]-4-pyridinamineYield 109.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 4.7 grams (50 milliliters) of 4-aminopyridine in 50 c.c. of dry pyridine was treated dropwise at room temperature with a solution of 6.6 grams of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylcarbonyl chloride (M. A. Davis, Stanley O. Winthrop, J. Steward, F. A. Sunahara, and F. Herr, J. Medicin. Chem. 1963, 6, 251-5) in 50 c.c. of toluene. After the exothermic reaction subsided the mixture was stirred at room temperature for 4 hours and was then poured into 30 c.c. of water. 100 milliliters of toluene were added and the phases were separated. The toluene phase was washed once with 100 c.c. of water, then the combined aqueous phases were back-extracted with toluene (3×100 c.c.). The combined toluene solutions were dried (MgSO4) and evaporated, leaving an oily residue which was evaporated several times with further toluene and finally once with ethanol to remove residual pyridine, giving 8.45 grams of a yellow solid. This solid was crystallised from toluene (charcoal) giving off-white crystals (4.78 g. 61%), mp 145°-6°; second crop, off-white crystals (0.96 g, 12%), mp 145°-7.5°.

Workup

  1. customAfter the exothermic reaction
  2. additionwas then poured into 30 c.c
  3. customthe phases were separated
  4. washThe toluene phase was washed once with 100 c.c
  5. extractionof water, then the combined aqueous phases were back-extracted with toluene (3×100 c.c.)
  6. dry with materialThe combined toluene solutions were dried (MgSO4)
  7. customevaporated
  8. customleaving an oily residue which
  9. customwas evaporated several times with further toluene
  10. customfinally once with ethanol to remove residual pyridine

Sources & evidence

ORD record
ord-522ccda7fbc34650b9418524a9cb6e79
Source dataset
uspto-grants-1984_08
Patent number
US04467091

Reaction notes

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