4-(2-Bromoethyl)phenol → 3-(R, S)-(1-cyano-1,1-diphenylmethyl)-1-(4-hydroxyphenethyl)-piperidine

HRID 21392

Reaction equation

HRID 21392 reaction equation
[C:1]([C:3]([CH: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].[OH:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]([C:3]([CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([OH:22])=[CH:24][CH:25]=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 842214-(2-Bromoethyl)phenolHCID 516892Sodium BicarbonateHCID 136337463-(R,S)-(1-cyano-1,1-diphenylmethyl)piperidine

Product 1

HCID 212240853-(R, S)-(1-cyano-1,1-diphenylmethyl)-1-(4-hydroxyphenethyl)-piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-(R,S)-(1-cyano-1,1-diphenylmethyl)piperidine (0.4 g), 4-hydroxyphenethyl bromide (0.32 g), sodium bicarbonate (0.5 g) and acetonitrile (15 ml) was heated under reflux for 4 hours. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (50 ml). The layers were separated and the aqueous layer extracted with dichloromethane (3×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum, yield 0.267 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (50 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with dichloromethane (3×20 ml)
  7. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a gum which
  10. customwas purified by column chromatography on silica eluting with dichloromethane
  11. additioncontaining methanol (5%)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c273441286654fe5903a6893d1e25104
Source dataset
uspto-grants-1995_06
Patent number
US05422358

Linked notes

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