Triethylamine → 2-Chloro-N-[4-[(6,11-dihydro-5H-dibenz[b,e]azepin5-yl)carbonyl]phenyl]benzeneacetamide

HRID 362386Notes

Reaction equation

HRID 362386 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:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][C:33](Cl)=[O:34].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][C:33]([NH:1][C:2]1[CH:3]=[CH:4][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:23][CH:24]=1)=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 182669Acetyl chloride, 2-(2-chlorophenyl)-2×HCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Product 1

HCID 676237892-Chloro-N-[4-[(6,11-dihydro-5H-dibenz[b,e]azepin5-yl)carbonyl]phenyl]benzeneacetamideYield 38.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.471 g (1.5 mmol) of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine, 0.340 g (1.8 mmol) of 2-chlorophenylacetyl chloride, 0.20 g of triethylamine and 9 mg of 4-(dimethylamino)pyridine in 10 ml of dichloromethane is stirred at room temperature for 48 hours. An additional 0.27 g of 2-chlorophenylacetyl chloride is added and the mixture stirred at room temperature for 2.5 hr. The mixture is washed with 1N HCl, H2O2, 1M NaHCO3, brine and dried (Na2SO4). The solvent is removed and the solid re-crystallized from dichloromethane to give 0.27 g of crystals, m.p. 191-194° C. Anal. Calc'd for C29H23ClN2O2 : C,74.6; H,5.0; N,6.0; Cl,7.6. Found: C,74.4; H,4.9; N,5.9; Cl,7.8.

Workup

  1. stirringthe mixture stirred at room temperature for 2.5 hr
  2. washThe mixture is washed with 1N HCl, H2O2, 1M NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is removed
  5. customthe solid re-crystallized from dichloromethane

Sources & evidence

ORD record
ord-006669fecc6943178e48b38aa8f9eeeb
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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