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

HRID 1448606Notes

Reaction equation

HRID 1448606 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH:8]1[C:18]2[CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[CH:13]([C:23](Cl)=O)[C:12]=2[CH:11]=[CH:10][CH:9]=1.O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH:8]1[C:18]2[CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[CH:13]([CH2:23][NH:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 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 1049PyridineSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 4.7 grams (50 milliliters) of 4-aminopyridine in 50 cc 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 cc of toluene. After the exothermic reaction subsided the mixture was stirred at room temperature for 4 hours and was then poured into 30 cc of water. 100 milliliters of toluene were added and the phases were separated. The toluene phase was washed once with 100 cc of water, then the combined aqueous phases were back-extracted with toluene (3×100 cc). 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. customthe phases were separated
  3. washThe toluene phase was washed once with 100 cc of water
  4. extractionthe combined aqueous phases were back-extracted with toluene (3×100 cc)
  5. customevaporated
  6. customleaving an oily residue which
  7. customwas evaporated several times with further toluene
  8. customfinally once with ethanol to remove residual pyridine

Sources & evidence

ORD record
ord-1a54b6418054400e854dfd5da7b937d6
Source dataset
uspto-grants-1979_12
Patent number
US04180670

Reaction notes

Loading…