Bromomethylcyclopropane → HCID 19367171, compound

HRID 1457770Notes

Reaction equation

HRID 1457770 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5](/[CH:6]=[CH:7]/[CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10]2)=[CH:4][CH:3]=1.BrC[CH:19]1[CH2:21][CH2:20]1>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:10]2[CH2:11][CH:19]2[CH2:21][CH2:20]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 19367166HCID 19367166, compound

Product 1

HCID 19367171HCID 19367171, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a reactor protected from moisture, there are introduced 2.3 g (0.010 mol) of (E)-2-(p-fluorocinnamyl)piperidine (Preparation 2B) dissolved in 25.2 ml acetonitrile, followed, during 2 min, by 1.56 g (1.1 ml-0.012 mol) bromomethylcyclopropane. The medium is kept stirring at ambient temperature for 1 h 30 min, is raised to 60° C. for 4 h, and is then lowered to 20°±3° C. for 16 h. The solvent is evaporated under vacuum and on a water bath. The oily residue is dissolved in water, acidified and extracted with ether. After decanting, the cooled aqueous phase is alkalinized with soda, extracted with ether and washed with saturated NaCl solution. The organic phase is dehydrated over Na2SO4 and the solvent is then removed by distillation. The residue is purified by the Chromatoflash technique, elution being carried out with a 90:10 v/v mixture of methylene chloride and 10% ammoniacal MeOH, and is then subjected to a second acid-alkali treatment. (E) -2-(p-fluorocinnamyl)-1-(cyclopropylmethyl)pyrrolidine is obtained in the form of a yellow oil.

Workup

  1. customIn a reactor protected from moisture, there
  2. temperatureis raised to 60° C. for 4 h
  3. waitis then lowered to 20°±3° C. for 16 h
  4. customThe solvent is evaporated under vacuum and on a water bath
  5. dissolutionThe oily residue is dissolved in water
  6. extractionextracted with ether
  7. customAfter decanting
  8. extractionextracted with ether
  9. washwashed with saturated NaCl solution
  10. customthe solvent is then removed by distillation
  11. customThe residue is purified by the Chromatoflash technique, elution
  12. additionbeing carried out with a 90:10 v/v mixture of methylene chloride and 10% ammoniacal MeOH

Sources & evidence

ORD record
ord-16d580fc80c346499f665a336644b178
Source dataset
uspto-grants-1998_12
Patent number
US05849760

Reaction notes

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