Hydrochloric Acid → (R)-1-(piperidin-3-yloxy)isoquinoline

HRID 1050503Notes

Reaction equation

HRID 1050503 reaction equation
[C:1]1([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.CC#N>[NH:14]1[CH2:15][CH2:16][CH2:17][C@@H:12]([O:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][N:2]=2)[CH2:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 118114503(R)-tert-butyl 3-(isoquinolin-1-yloxy)piperidine-1-carboxylate

Product 1

HCID 118115704(R)-1-(piperidin-3-yloxy)isoquinoline

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 53 was treated with 4N HCl in dioxane (40 mL) at RT for 3 h. The mixture was concentrated in vacuo to give a viscous oil which was dissolved in MeCN (200 mL). To the solution was added NaHCO3 powder (2.0 g). The mixture was stirred at RT overnight. The mixture was filtered and the filtrate was concentrated. The residue was subjected to flash column chromatography with 0%-100% EtOAc in DCM and then 0%-9% MeOH in DCM to isolate (R)-1-(piperidin-3-yloxy)isoquinoline (54).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a viscous oil which
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a69c4af49733466f9e5846f3041c8538
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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