Decalin → HCID 9933189, compound

HRID 2304361Notes

Reaction equation

HRID 2304361 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[C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=1.[OH-].[K+].C1C2C(CCCC2)CCC1>[Cu].C(Cl)(Cl)Cl>[I:27][C:24]1[CH:25]=[CH:26][C:21]([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:22][CH:23]=1

Participants

7

Reactant 4

HCID 7044DecalinHCID 115221-Bromo-4-iodobenzeneHCID 14797Potassium HydroxideHCID 112995199H-Tribenzo[b,d,f]azepine

Product 1

HCID 9933189HCID 9933189, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
200 °C

Procedure

Eighteen point two (18.2) grams (75 mmol) of 9H-tribenz[b,d,f]azepin, 63.7 g (225 mmol) of 1-bromo-4-iodo-benzene, 5.0 g (90 mmol) of potassium hydroxide, and 2.0 g (31 mmol) of a copper powder were mixed with 50 ml of decalin and stirred by heating under a nitrogen gas current for about one week at outer temperature of 200° C. After the temperature of the reaction solution was lowered to near room temperature, chloroform was added thereto, and the solution was filtered through Celite to remove insoluble matters. Water was added to the filtrate, and the solution was subjected to extraction. The obtained concentrated reaction product was purified by silica gel column chromatography to obtain 17.4 g of 9-(4-iodophenyl)-tribenz[b,d,f]azepin (yield: 52%, a small amount of 4-bromophenyl compound was contained).

Workup

  1. customwas lowered to near room temperature
  2. filtrationthe solution was filtered through Celite
  3. customto remove insoluble matters
  4. additionWater was added to the filtrate
  5. extractionthe solution was subjected to extraction
  6. concentrationThe obtained concentrated
  7. customreaction product
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b3b984430dc4b5189693cb31f1b251f
Source dataset
uspto-grants-2002_08
Patent number
US06436558B1

Reaction notes

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