1-Bromooctane → HCID 67314889, compound

HRID 1012558Notes

Reaction equation

HRID 1012558 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:12]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 67314889HCID 67314889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under the atmosphere of nitrogen, 4 parts of 1,2,3,4-tetrahydroquinoline, 6.4 parts of 1-bromooctane, 5 parts of dimethylformamide (DMF), and 5 parts of potassium carbonate were stirred at 130° C. for 4 hours. After the reaction, the resultant was extracted with water/ethyl acetate, and the ethyl acetate phase was dried over magnesium sulfate. Ethyl acetate was distilled off, and the residue was separated and purified by column chromatography to yield 3 parts of a precursor of the compound (301), 1,2,3,4-tetrahydro-1-octylquinoline as a colorless liquid. Next, 1.7 parts of phosphorus oxychloride were dropwise added to 10 parts of chloroform and 1 part of N,N-dimethylacrolein, the temperature of which was adjusted to 5° C., while the temperature of the reaction solution was kept at 10° C. or lower. The reaction solution was then stirred at 5° C. for 1 hour. Thereafter, 2.5 parts of 1,2,3,4-tetrahydro-1-octylquinoline described above were added thereto, and then the reactive components were caused to react at 25° C. for 1 hour. The reaction solution was then stirred at 70° C. for 1 hour. Thereafter, a 20% solution of sodium hydroxide in water was added to the reaction solution until the pH turned to 12. The precipitated crystal was filtrated, and the resultant crystal was washed with water. The crystal was then separated by column chromatography (hexane/ethyl acetate), and recrystallized from ethanol to yield 2.7 parts of the compound (301) as a yellow crystal.

Workup

  1. customAfter the reaction
  2. extractionthe resultant was extracted with water/ethyl acetate
  3. dry with materialthe ethyl acetate phase was dried over magnesium sulfate
  4. distillationEthyl acetate was distilled off
  5. customthe residue was separated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-a9c5165313ff4243bdc76af771056c5b
Source dataset
uspto-grants-2011_07
Patent number
US07977570B2

Reaction notes

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