[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester → 1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine

HRID 913062Notes

Reaction equation

HRID 913062 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH3:25])[CH:16]=2)[CH2:10][CH2:9]1)(C)(C)C>C(O)C.Cl.O1CCOCC1>[CH2:24]([O:23][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH3:22])[CH2:14][N:11]1[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]1)[CH3:25]

Participants

5

Reactant 1

HCID 67147361[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamineYield 89%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of [1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (9.71 g, 26.64 mmol) in ethanol (50 mL) and 4 M HCl in dioxane (75 mL) was stirred at rt for 2 h. The hydrochloric acid was removed under reduced pressure and the crude reaction product extracted from a solution of 1 M NaOH (200 mL) with ethyl acetate (3×100 mL). The combined organic phases were dried over MgSO4 and concentrated by evaporation under reduced pressure yielding 4.69 g (89%) of a white solid. The crude material was directly used in the following reaction step. MS (ESI): 265.0 [M+H]+.

Workup

  1. customThe hydrochloric acid was removed under reduced pressure
  2. customthe crude reaction product
  3. extractionextracted from a solution of 1 M NaOH (200 mL) with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1e82de961db0464f873556d30e889c5b
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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