1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 654095Notes

Reaction equation

HRID 654095 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.BrCCCCl.C1(C2CCNCC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 2036891-(3-Chloropropyl)-4-phenylpiperidine

Product 1

HCID 98375831-(3-Chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Chloropropyl)-4-phenyl-1,2,4,6-tetrahydropyridine can be prepared as follows: a solution of 1-bromo-3-chloropropane (6 cc) and 4-phenyl-1,2,3,6-tetrahydropyridine (5.1 g) in acetonitrile (60 cc) is stirred at 25° C. for 20 hours with potassium carbonate (97 g). The mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height) and eluted with a mixture of cyclohexane and ethyl acetate (50--50 by volume), 250-cc fractions being collected. Fractions 7 to 13 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (5 g) in the form of a yellow oil.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height)
  4. washeluted with a mixture of cyclohexane and ethyl acetate (50--50 by volume), 250-cc fractions
  5. custombeing collected
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-b29375861d594433a16ffd83ce2d1d0a
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

Loading…