1-Chloro-3-methyl-2-butene → HCID 21328434, compound

HRID 1282889Notes

Reaction equation

HRID 1282889 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[CH3:5].C(=O)([O-])[O-].[K+].[K+].[Cl:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29]>C1C=CC=CC=1>[ClH:25].[CH3:1][N:2]([CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[CH3:5])[CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 104291-Chloro-3-methyl-2-buteneHCID 11430Potassium CarbonateHCID 21328441HCID 21328441, compound

Product 1

HCID 21328434HCID 21328434, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 23.9 g. of N-Methyl-2-(3-phenoxyphenyl)propylamine, prepared according to the method of Example 20, and 13.8 g. of potassium carbonate in benzene was treated with 20.8 g. of 1-chloro-3-methyl-2-butene. The reaction mixture was refluxed with mechanical stirring for about 60 hours. After cooling to room temperature, the reaction was washed with water and extracted with dilute hydrochloric acid. The acidic extract was basified with sodium hydroxide solution and extracted with ether. The ether extract was washed twice with water and dried over sodium sulfate. Dry hydrogen chloride gas was passed into the ethereal solution and the resulting precipitated hydrochloride salt was filtered and recrystallized from an alcohol-ether mixture to yield 11.5 g. of the titled product, m.p. 120°-122°C., pK'a 8.5.

Workup

  1. additionA mixture of 23.9 g
  2. temperatureThe reaction mixture was refluxed
  3. washthe reaction was washed with water
  4. extractionextracted with dilute hydrochloric acid
  5. extractionThe acidic extract
  6. extractionextracted with ether
  7. extractionThe ether extract
  8. washwas washed twice with water
  9. dry with materialdried over sodium sulfate
  10. customthe resulting precipitated hydrochloride salt
  11. filtrationwas filtered
  12. customrecrystallized from an alcohol-ether mixture
  13. customto yield 11.5 g

Sources & evidence

ORD record
ord-abd9fcded39149a0ae43d6346f5ce4fe
Source dataset
uspto-grants-1976_08
Patent number
US03972934

Reaction notes

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