Triethylamine → HCID 15307979, compound

HRID 355890Notes

Reaction equation

HRID 355890 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.Cl.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH:19]1[C:10]2[CH2:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[CH2:14][N:8]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:26]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[O:33])=[CH:24][CH:23]=3)=[O:7])[C:9]=2[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Product 1

HCID 15307979HCID 15307979, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.628 g (2 mmol) of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine, 0.551 g (3 mmol) of nicotinoyl chloride, hydrochloride, 0.606 g (6 mmol) of triethylamine and 15 mg of 4-(dimethylamino)pyridine in 17 ml of dichloromethane is refluxed for 7 hours. The mixture is washed with H2O, 2N citric acid, H2O, 1N NaHCO3, brine and dried (Na2SO4). The solvent is removed and the solid recrystallized from hexane-dichloromethane to give 0.12 g of crystals,. m.p. 217°-220° C. Anal Calc'd for C27H21N3O2H2O: C,74.1; H,5.3; N,9.6. Found: 73.6; H,4.7; N,9.8.

Workup

  1. temperatureis refluxed for 7 hours
  2. washThe mixture is washed with H2O, 2N citric acid, H2O, 1N NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is removed
  5. customthe solid recrystallized from hexane-dichloromethane

Sources & evidence

ORD record
ord-e7488e8153ec4918b86338e03d2eb768
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

Loading…