4-Methoxybenzoic Acid → HCID 118115261, compound

HRID 1050607Notes

Reaction equation

HRID 1050607 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15](O)(=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.O1CCOCC1.CCOC(C)=O>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)=[O:24])=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 74784-Methoxybenzoic AcidHCID 81531DiisopropylethylamineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 2724699PyBOP

Product 1

HCID 118115261HCID 118115261, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 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.

Workup

  1. stirringThe mixture was stirred at RT for 3 hours
  2. washwashed with water 60 mL×3
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3db824b8c85d47618ec18f4b4863097a
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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