2-(Phenylmethyl)oxirane → HCID 21837497, compound

HRID 1292143Notes

Reaction equation

HRID 1292143 reaction equation
[C:1]1([C:7]2([C:13]#[N:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:15]1[CH2:24][CH:16]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1>[OH:15][CH:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:24][N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:13]#[N:14])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 948262-(Phenylmethyl)oxiraneHCID 1811384-Piperidinecarbonitrile, 4-phenyl-

Product 1

HCID 21837497HCID 21837497, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-phenyl-piperidine-4-carbonitrile (6.3 g, 34 mmol) and (2.3-epoxypropyl)benzene (5.0 g, 37 mmol) in dioxane was refluxed for seven days. The solvent was evaporated and the residue was shaken between dilute sodium hydroxide and diethyl ether. The ether extract was dried over potassium carbonate, filtered and the product was converted to the hydrochloride as described in Example 5. Recrystallization from a mixture of ethanol and acetonitrile gave 10.0 g with m.p. 246°-249° C.

Workup

  1. temperaturewas refluxed for seven days
  2. customThe solvent was evaporated
  3. extractionThe ether extract
  4. dry with materialwas dried over potassium carbonate
  5. filtrationfiltered
  6. customRecrystallization
  7. additionfrom a mixture of ethanol and acetonitrile
  8. customgave 10.0 g with m.p. 246°-249° C.

Sources & evidence

ORD record
ord-44ab26c2be5f4e5395352559b8677c75
Source dataset
uspto-grants-1998_05
Patent number
US05756520

Reaction notes

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