Triethylamine → 3-chloro-1-(9H-tribenz[b,d,f]azepine-9-yl)propan-1-one

HRID 861897Notes

Reaction equation

HRID 861897 reaction equation
[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[NH:8][C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=3[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:20][CH2:21][CH2:22][C:23](Cl)=[O:24].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:20][CH2:21][CH2:22][C:23]([N:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[CH:19]=[CH:18][CH:17]=[CH:16][C:7]1=2)=[O:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 516892Sodium BicarbonateHCID 112995199H-Tribenzo[b,d,f]azepine

Product 1

HCID 189171693-chloro-1-(9H-tribenz[b,d,f]azepine-9-yl)propan-1-oneYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9H-Tribenz[b,d,f]azepine (0.17 g, 0.70 mmol, prepared similarly as described by H. C. Axtell et al., J. Org. Chem. 56, 3906 (1991)) was suspended in dry toluene (5 ml). 3-Chloropropionyl chloride (0.13 g, 1.0 mmol) and triethylamine (0.1 ml) were added and the mixture was heated at reflux temperature for 1.5 hour. Saturated aqueous sodium bicarbonate (10 ml) was added, and the phases were separated. The organic phase was washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo, affording 220 mg, (94%) of crude 3-chloro-1-(9H-tribenz[b,d,f]azepine-9-yl)propan-1-one as a foam.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 1.5 hour
  3. customthe phases were separated
  4. washThe organic phase was washed with brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-389372046bb14407b7543b0b2c5210e3
Source dataset
uspto-grants-1998_02
Patent number
US05716949

Reaction notes

Loading…