1,2,3,6-Tetrahydro-4-phenylpyridine → 4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butyne

HRID 53641Notes

Reaction equation

HRID 53641 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][C:7]#[CH:8])(=O)=O.[C:16]1([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:16]1([C:22]2[CH2:27][CH2:26][N:25]([CH2:8][CH2:7][C:6]#[CH:5])[CH2:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 2720203-Butynyl p-toluenesulfonateHCID 516892Sodium Bicarbonate

Product 1

HCID 107985574-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butyne

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-butynyl tosylate (25.0 g, 0.11 mol), 4-phenyl-1,2,3,6-tetrahydropyridine (21.8 g, 0.11 mol) and sodium bicarbonate (10.3 g, 0.12 mol) in 300 mL of dimethylformamide is heated at 80° C. for 18 hours. The solvent is removed under reduced pressure, and the residue is partitioned between 200 mL of dichloromethane and 200 mL of water. The aqueous layer is extracted with 100 mL of dichloromethane and the combined organic layers are dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 25% ethyl acetate/75% hexane) to give the title compound as a yellow solid; mp 36.5°-37.5° C.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is partitioned between 200 mL of dichloromethane and 200 mL of water
  3. extractionThe aqueous layer is extracted with 100 mL of dichloromethane
  4. dry with materialthe combined organic layers are dried (sodium sulfate)
  5. customthe solvent is removed in vacuo
  6. customThe residue is chromatographed (silica gel, 25% ethyl acetate/75% hexane)

Sources & evidence

ORD record
ord-f5c0983a1e764e1899d3598335b39e0d
Source dataset
uspto-grants-1997_04
Patent number
US05620988

Reaction notes

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