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

HRID 1290659
Notes
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Reaction equation

HRID 1290659 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 1140
Toluene
Solvent

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-dab7323260b842c58c0651648daf788f
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05753643

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes