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

HRID 128948Notes

Reaction equation

HRID 128948 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 9el, 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 9el, 25% ethyl acetate/75% hexane)

Sources & evidence

ORD record
ord-e103df3082474251a0fdaf2f6d2182ad
Source dataset
uspto-grants-1995_11
Patent number
US05466698

Reaction notes

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