1,2,3,6-Tetrahydro-4-phenylpyridine → HCID 15166841, compound

HRID 892458Notes

Reaction equation

HRID 892458 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH2:10]Cl)=[CH:3][CH:2]=1.[C:12]1([C:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH:23]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[K+]>C(#N)C>[C:12]1([C:18]2[CH2:23][CH2:22][N:21]([CH2:10][CH2:9][CH2:8][CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 516893Potassium BicarbonateHCID 109539414-(4-Chlorobutyl)pyridine

Product 1

HCID 15166841HCID 15166841, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(4-pyridinyl)-1-butylchloride (Example A) (0.76 g, 4.47 mmol), 1,2,3,6-tetrahydro-4-phenylpyridine (0.796 g, 5.0 mmol), and potassium bicarbonate (1.0 g, 10 mmol) in 5 mL of acetonitrile are heated to reflux for 8 hours. The reaction is cooled to room temperature and the acetonitrile removed in vacuo. The residue is partitioned between 50 mL of water and 50 mL of chloroform. The aqueous layer is extracted again with 50 mL of chloroform and the combined organic extracts are dried over sodium sulfate and the solvent removed in vacuo. The resulting residue is chromatographed on silica gel (2% to 3% methanol, 0.1% ammonia, chloroform) to obtain 1.10 g of 4-[4-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)-butyl]pyridine as a white solid; mp 89°-90° C.

Workup

  1. temperatureare heated
  2. temperatureto reflux for 8 hours
  3. customthe acetonitrile removed in vacuo
  4. customThe residue is partitioned between 50 mL of water and 50 mL of chloroform
  5. extractionThe aqueous layer is extracted again with 50 mL of chloroform
  6. dry with materialthe combined organic extracts are dried over sodium sulfate
  7. customthe solvent removed in vacuo
  8. customThe resulting residue is chromatographed on silica gel (2% to 3% methanol, 0.1% ammonia, chloroform)

Sources & evidence

ORD record
ord-90b80fc0ce844897ad98a4c54382f8ec
Source dataset
uspto-grants-1992_06
Patent number
US05118691

Reaction notes

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