Carbon Dioxide → HCID 18671357, compound

HRID 1057291Notes

Reaction equation

HRID 1057291 reaction equation
[CH:1]1([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:15]Br.C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 24408BromineHCID 15707007N-Phenylcycloheptanamine

Product 1

HCID 18671357HCID 18671357, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

18.9 g N-cycloheptyl aniline (XXIV) (CA registration number [61142-86-7], see Synthesis, 1991, 11:1043-1045 for its preparation), 32.1 g tetrabutylammonium bromide [(C4H9)4N+Br−] and 100 ml methylene chloride (CH2Cl2) were placed into a three-necked flask and cooled down to 0° C. with iced saline. 15.8 g bromine (Br2) was dropped slowly with stirring and was stirred for 4 hours while maintaining at 0° C. The temperature was allowed to raise to room temperature and saturated sodium carbonate solution was dropped slowly till evolution of carbon dioxide ceased. Water layer was separated and extracted with methylene chloride for three times. The organic layers were combined and the solvent evaporated. The residue was recrystalized from 95% ethanol for two times to yield 21.4 g 4bromo-N-cycloheptyl aniline (XXV).

Workup

  1. stirringwas stirred for 4 hours
  2. temperaturewhile maintaining at 0° C
  3. temperatureto raise to room temperature
  4. customWater layer was separated
  5. extractionextracted with methylene chloride for three times
  6. customthe solvent evaporated
  7. customThe residue was recrystalized from 95% ethanol for two times

Sources & evidence

ORD record
ord-6015d98f65df45fcb3b28d90450b79fe
Source dataset
uspto-grants-2003_02
Patent number
US06514956B1

Reaction notes

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