Pyridine → Phenylmethyl 3′,6′-dihydro[2,4′-bipyridine]-1′(2′H)-carboxylate

HRID 2256071Notes

Reaction equation

HRID 2256071 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](O)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>ClCCl.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 22221502Benzyl 4-hydroxy-4-(pyridin-2-yl)piperidine-1-carboxylate

Product 1

HCID 19029119Phenylmethyl 3′,6′-dihydro[2,4′-bipyridine]-1′(2′H)-carboxylateYield 63.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-hydroxy-4-(2-pyridyl)piperidine (0.8 g) in 20 mL of dichloromethane at 0° C. was treated with pyridine (2 mL) followed by thionyl chloride (0.22 mL). The reaction mixture was allowed to warm to the room temperature and stirred for 16 hours. At the end of this period, the reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was washed with a solution of copper sulfate, dried over magnesium sulfate and concentrated under reduce pressure to obtain the crude material. This material was purified by column chromatography; elution with 1:1 hexane:ethylacetate afforded the named product (0.48 g); MS: 295; NMR: 2.67 (m, 2), 3.74 (m, 2), 4.2 (m, 2), 5.18 (s, 2), 6.6 (m, 1), 7.18 (m, 1), 7.36 (m, 6), 7.68 (m, 1), 8.56 (m, 1).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed with a solution of copper sulfate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain the crude material
  6. customThis material was purified by column chromatography
  7. washelution with 1:1 hexane

Sources & evidence

ORD record
ord-0769971184144e178f368c8abd0588d0
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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