Hydrochloric Acid → HCID 86681868, compound

HRID 1749373Notes

Reaction equation

HRID 1749373 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][C@H:10]2[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([CH3:23])[CH2:12][CH2:11]2)[CH:4]=1)#[N:2].[ClH:24]>C(Cl)Cl>[ClH:24].[CH3:23][C@H:13]1[NH:14][CH2:15][C@H:10]([O:9][C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][N:6]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86681867HCID 86681867, compound

Product 1

HCID 86681868HCID 86681868, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (2R,5R)-5-[(4-cyanopyridin-2-yl)oxy]-2-methylpiperidine-1-carboxylate (5.42 g, 17.1 mmol) in CH2Cl2 (8 mL) was cooled at −78° C. and treated with HCl (4 M in dioxane, 30 mL, 120 mmol). The reaction was allowed to warm to RT. After 40 mins, the reaction was concentrated in vacuo and the resulting residue was slurried in Et2O for several hours. The resulting mixture was filtered and the solids washed with Et2O, providing the crude titled compound which was used without further purification. LRMS m/z (M+H) 218.3 found, 218.1 required.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. waitthe resulting residue was slurried in Et2O for several hours
  3. filtrationThe resulting mixture was filtered
  4. washthe solids washed with Et2O

Sources & evidence

ORD record
ord-fa4b2b41a9fb4b9e96fe313f6ed40b6f
Source dataset
uspto-grants-2015_10
Patent number
US09156819B2

Reaction notes

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