Hydrochloric Acid → 3-Methyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine hydrochloride

HRID 1666399Notes

Reaction equation

HRID 1666399 reaction equation
[CH3:1][C:2]1[C:3]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[ClH:29].O1CCOCC1>C(Cl)Cl>[ClH:29].[CH3:1][C:2]1[C:3]([O:8][C:9]2[CH:28]=[CH:27][CH:26]=[C:11]([CH:12]=[C:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68949881tert-Butyl 4-(3-(3-methylpyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 668760903-Methyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(3-(3-methylpyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (3.9 g, 10 mmol) from Step 4 was dissolved in CH2Cl2 (50 mL) and treated with HCl in dioxane (20 mL, 4.0 M, 80 mmol). After 16 h the reaction was concentrated in vacuo to provide the title compound as a white solid (3.6 g).

Workup

  1. concentrationAfter 16 h the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-0696f7d4c0f240aa91e32053e71106fe
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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