1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-4-phenylpiperidine

HRID 654107Notes

Reaction equation

HRID 654107 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:17][CH2:16][CH2:15][CH2:14][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 698734-Phenylpiperidine

Product 1

HCID 2036891-(3-Chloropropyl)-4-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Chloropropyl)-4-phenylpiperidine can be obtained as follows: a solution of 4-phenylpiperidine (8 g) and of 1-bromo-3-chloropropane (20 cc) in acetonitrile (80 cc) is stirred at 25° C. for 24 hours with potassium carbonate (28 g). The mixture is filtered and is then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.06-0.2-mm particle size, 3-cm diameter, 25-cm height) and eluted with a mixture of cyclohexane and ethyl acetate (50--50 by volume), 60-cc fractions being collected. Fractions 6 to 10 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 1-(3-Chloropropyl)-4-phenylpiperidine (8 g) is obtained in the form of oil.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationis then concentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on a column of silica gel (0.06-0.2-mm particle size, 3-cm diameter, 25-cm height)
  4. washeluted with a mixture of cyclohexane and ethyl acetate (50--50 by volume), 60-cc fractions
  5. custombeing collected
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-96a595aedfb947aaa9c169f686fd59c4
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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