Decalin → HCID 22501123, compound

HRID 2227126Notes

Reaction equation

HRID 2227126 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.[Br:20][C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1.[OH-].[K+].C1C2C(CCCC2)CCC1>[Cu].C(Cl)(Cl)Cl>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([N:8]2[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[CH:19]=[CH:18][CH:17]=[CH:16][C:7]2=3)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7044DecalinHCID 78041,4-DibromobenzeneHCID 14797Potassium HydroxideHCID 112995199H-Tribenzo[b,d,f]azepine

Product 1

HCID 22501123HCID 22501123, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 9.2 g (38 mmol) of 9H-tribenz[b,d,f]azepine (synthesized in accordance with J. Org. Chem., vol. 56, p. 3906 (1991)), 44.8 g (190 mmol) of 1,4-dibromobenzene, 5.6 g (100 mmol) of potassium hydroxide, 1.6 g (25 mmol) of copper powder, and 50 ml of decalin was heated at an external temperature of 200° C. for 36 hours in a nitrogen stream while stirring. The reaction mixture was cooled nearly to room temperature, chloroform was added thereto, followed by filtration using Celite to remove the insoluble matter. The filtrate was concentrated. To remove decalin, n-hexane was added to the residue, followed by filtration. The filter cake was purified by silica gel column chromatography to give 3.8 g (25%) of 9-(4-bromophenyl)-9H-tribenz[b,d,f]azepine.

Workup

  1. temperatureThe reaction mixture was cooled nearly to room temperature
  2. filtrationfollowed by filtration
  3. customto remove the insoluble matter
  4. concentrationThe filtrate was concentrated
  5. customTo remove decalin, n-hexane
  6. additionwas added to the residue
  7. filtrationfollowed by filtration
  8. customThe filter cake was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3c9982081c44f9597bec9d3655c8635
Source dataset
uspto-grants-2002_07
Patent number
US06413657B1

Reaction notes

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