Sodium Hydroxide → N-[3-(methyloxy)-4-piperidinyl]benzamide

HRID 2168198Notes

Reaction equation

HRID 2168198 reaction equation
[CH3:1][O:2][CH:3]1[CH:8]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.[OH-].[Na+]>Cl.O1CCOCC1.O>[CH3:1][O:2][CH:3]1[CH:8]([NH:9][C:10](=[O:11])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6][NH:5][CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 679880741,1-Dimethylethyl 3-(methyloxy)-4-[(phenylcarbonyl)amino]-1-piperidinecarboxylate

Product 1

HCID 19883474N-[3-(methyloxy)-4-piperidinyl]benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-(methyloxy)-4-[(phenylcarbonyl)amino]-1-piperidinecarboxylate D20 (4.0 g) in HCl/1,4-dioxane (30 ml) was stirred at room temperature for overnight. The resulting mixture was dissolved in water (50 ml) and basified with sodium hydroxide to pH 10.0 then extracted with DCM (3×100 ml). The organic layer was dried over anhydrous MgSO4, concentrated in vacuo to desired product D21 as an oil in 500 mg. LCMS [MH+] [email protected] and 1.19 (isomers) (5 min run)

Workup

  1. extractionthen extracted with DCM (3×100 ml)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo to desired product
  4. customLCMS [MH+] [email protected] and 1.19 (isomers) (5 min run)

Sources & evidence

ORD record
ord-acd487817397493a9a6639a0d0fd745f
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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