Hydrochloric Acid → HCID 118115143, compound

HRID 1050608Notes

Reaction equation

HRID 1050608 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)=[O:8])=[CH:5][CH:4]=1.[ClH:25]>O1CCOCC1>[ClH:25].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[O:8])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118115261HCID 118115261, compound

Product 1

HCID 118115143HCID 118115143, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-tert-Butyl 3-aminopiperidine-1-carboxylate (1.70 g, 8.5 mmol) was mixed with p-anisic acid (1.42 g, 9.35 mmol) in 5 mL DMF and 25 mL dioxane. The mixture was stirred at RT, and to it were added DIEA (2.07 mL, 11.9 mmol) and then PyBOP (4.86 g, 9.35 mmol). The mixture was stirred at RT for 3 hours, diluted with 150 mL EtOAc, washed with water 60 mL×3, dried, concentrated, subjected to silica flash column using 0 to 20% EtOAc in DCM to isolate (R)-tert-butyl 3-(4-methoxybenzamido)piperidine-1-carboxylate (488) in quantitative yield. Compound 488 (1.86 g, 5.56 mmol) was treated with 30 mL commercial 4N HCl in dioxane at RT for 15 min, giving (R)-4-methoxy-N-(piperidin-3-yl)benzamide hydrochloride (489) in quantitative yield as a white solid.

Sources & evidence

ORD record
ord-b89f362f5ddc432e9cb3b3d34f2ef457
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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