Potassium Carbonate → 3-(R)-(1-cyano-1,1-diphenylmethyl)-1--(3,4-dichlorophenethyl)piperidine

HRID 21390Notes

Reaction equation

HRID 21390 reaction equation
[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:26][CH2:27]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:27][CH2:26][C:25]2[CH:29]=[CH:30][C:31]([Cl:32])=[C:23]([Cl:22])[CH:24]=2)[CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 151493894-(2-Bromoethyl)-1,2-dichlorobenzeneHCID 228537583-(R)-(1-cyano-1,1-diphenylmethyl)-piperidine

Product 1

HCID 213113123-(R)-(1-cyano-1,1-diphenylmethyl)-1--(3,4-dichlorophenethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-(R)-(+)-(1-cyano-1,1-diphenylmethyl)piperidine (0.28 g), 3,4-dichlorophenethyl bromide (0.255 g), anhydrous potassium carbonate (0.3 g) and acetonitrile (10 ml) was heated under reflux for 8 hours. The mixture was partitioned between dichlorometbane (30 ml) and 10% aqueous potassium carbonate (20 ml), the layers separated and the aqueous layer extracted with dichloromethane (3×70 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated inn vacuo to give an oil which was purified by column chromatograpby on silica eluting with dichloromethane containing hexane (30%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was crystallised from acetonitrile to give the title compound, yield 0.233 g, m.p. 139°-142° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. customThe mixture was partitioned between dichlorometbane (30 ml) and 10% aqueous potassium carbonate (20 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (3×70 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated inn vacuo
  8. customto give an oil which
  9. customwas purified by column chromatograpby on silica eluting with dichloromethane
  10. additioncontaining hexane (30%)
  11. concentrationconcentrated in vacuo
  12. customto give an oil which
  13. customwas crystallised from acetonitrile

Sources & evidence

ORD record
ord-2b313ee99fad42879db9e4efd08876bc
Source dataset
uspto-grants-1995_06
Patent number
US05422358

Reaction notes

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