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

HRID 1456238Notes

Reaction equation

HRID 1456238 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, H2O, 1M NaHCO3, brine and dried (Na2SO4). The solvent is removed and the solid recrystallized from dichloromethane to give 0.27 g of crystals;, m.p. 191°-194° C.

Workup

  1. stirringthe mixture stirred at room temperature for 2.5 hr
  2. washThe mixture is washed with 1N HCl, H2O, 1M NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is removed
  5. customthe solid recrystallized from dichloromethane

Sources & evidence

ORD record
ord-045c2b8ed7874063b70dcbe08175ec48
Source dataset
uspto-grants-1998_12
Patent number
US05843952

Reaction notes

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