Potassium Carbonate → HCID 22099470, compound

HRID 1457604Notes

Reaction equation

HRID 1457604 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[CH:17]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)P(N(C)C)(N(C)C)=O>[CH:17]1([NH:13][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16992BromocycloheptaneHCID 853464-Octylaniline

Product 1

HCID 22099470HCID 22099470, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 10.0 g of 4-octylaniline, 8.6 g of bromocyclo-heptane, 13.5 g of potassium carbonate and 50 ml of hexamethylphosphoramide (HMPA) was stirred at 90° to 100° C. for 7 hours. After cooling, a saturated saline solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=50:1) to give 7.79 g of N-cycloheptyl-N-(4-octylphenyl)amine (yield: 53%, brown oily product, IR (film): 3390, 2925, 2854, 1617, 1518 cm-1).

Workup

  1. temperatureAfter cooling
  2. additiona saturated saline solution was added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-91ede66500334df4bf41e81a0a0b3ac2
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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