[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester → 1-(4-Chloro-3-ethoxybenzyl)piperidin-4-ylamine

HRID 2242958Notes

Reaction equation

HRID 2242958 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]([Cl:21])=[C:17]([O:22][CH2:23][CH3:24])[CH:16]=2)[CH2:10][CH2:9]1)(C)(C)C>C(O)C.Cl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]2)=[CH:16][C:17]=1[O:22][CH2:23][CH3:24]

Participants

4

Reactant 1

HCID 67147374[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 592103771-(4-Chloro-3-ethoxybenzyl)piperidin-4-ylamineYield 57%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of [1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.78 g, 2.12 mmol) in ethanol (10 mL) and 4 M HCl (15 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 (50 mL) with ethyl acetate (3×50 mL). The combined organic phases were dried over MgSO4 and concentrated by evaporation under reduced pressure yielding 0.32 g (57%) of a white solid. The crude material was directly used in the following reaction step. MS (ISP): 269.0 [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 (50 mL) with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b6122717f70846098492e64b5aad79a6
Source dataset
uspto-grants-2010_03
Patent number
US07674804B2

Reaction notes

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