Acetic Acid → Ethyl 4-(4-aminopiperidin-1-yl)benzoate

HRID 591607Notes

Reaction equation

HRID 591607 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)=[N+]=[N-].C(O)(=O)C.O.[H][H]>O1CCOCC1.[Pd]>[NH2:1][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 86662016Ethyl 4-(4-azidopiperidin-1-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 22557718Ethyl 4-(4-aminopiperidin-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 4-(4-azidopiperidin-1-yl)benzoate (7.62 g, 27.8 mmol) in dioxane (190 mL) was added acetic acid (27 mL) and water (54 mL). Then, 10% Pd/C (0.750 g) was added and the mixture was hydrogenated under 1 atmosphere of hydrogen for 5 hours. The mixture was filtered through Celite, concentrated, and 0.5 M HCl (500 mL) was added. The solution was washed with ethyl acetate (2×300 mL) and the aqueous phase basified with ammonium hydroxide, to pH 12. The aqueous phase was saturated with sodium chloride, extracted with CH2Cl2 (2×300 mL), dried over anhydrous MgSO4, filtered, and concentrated, to afford ethyl 4-(4-aminopiperidin-1-yl)benzoate.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. addition0.5 M HCl (500 mL) was added
  4. washThe solution was washed with ethyl acetate (2×300 mL)
  5. extractionextracted with CH2Cl2 (2×300 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c5b85f3d37d402e94e84bc30f22520c
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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