Piperidine → HCID 19007202, compound

HRID 1614557Notes

Reaction equation

HRID 1614557 reaction equation
[Cl:1][CH2:2][Si:3]([CH3:13])([CH3:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1(C)C(C)=CC=CC=1>[ClH:1].[CH3:12][Si:3]([CH2:2][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)([CH3:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 22399687(Chloromethyl)[(2-fluorophenyl)methyl]dimethylsilane

Product 1

HCID 19007202HCID 19007202, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution containing 10.8 g of chloromethyldimethyl-(2-fluorobenzyl)silane and 10.6 g of piperidine in 40 ml of xylene is refluxed for 5.5 hours, then cooled down and washed 5 times with a total of 250 ml of water. After drying the organic phase over anhydrous magnesium sulfate and filtering off the drying agent, the filtrate is evaporated to solvent-free. The oily pale yellow residue is dissolved in 40 ml of methyl ethyl ketone and acidified to pH 4.5 by adding methanolic hydrogen chloride solution. 15 ml of solvent are distilled off from the solution under atmospheric pressure, the crystalline precipitate obtained is filtered at 0° C. and dried to give 13.1 g (87%) of the named product, m.p.: 203°-205° C.

Workup

  1. temperatureis refluxed for 5.5 hours
  2. temperaturecooled down
  3. washwashed 5 times with a total of 250 ml of water
  4. dry with materialAfter drying the organic phase over anhydrous magnesium sulfate
  5. filtrationfiltering off the drying agent
  6. customthe filtrate is evaporated to solvent-free
  7. dissolutionThe oily pale yellow residue is dissolved in 40 ml of methyl ethyl ketone
  8. additionby adding methanolic hydrogen chloride solution
  9. distillation15 ml of solvent are distilled off from the solution under atmospheric pressure
  10. customthe crystalline precipitate obtained
  11. filtrationis filtered at 0° C.
  12. customdried

Sources & evidence

ORD record
ord-82da6f712add42519ef58305f5be15fa
Source dataset
uspto-grants-1993_03
Patent number
US05198446

Reaction notes

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