Hydrochloric Acid → 3-(4-Amino-piperidin-1-yl)-butyronitrile

HRID 1257612Notes

Reaction equation

HRID 1257612 reaction equation
Cl.C(OC(=O)[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH:15]([CH3:19])[CH2:16][C:17]#[N:18])[CH2:11][CH2:10]1)(C)(C)C>O1CCOCC1>[NH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH:15]([CH3:19])[CH2:16][C:17]#[N:18])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 47371556[1-(2-Cyano-1-methyl-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 609133153-(4-Amino-piperidin-1-yl)-butyronitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
45 °C

Procedure

A 4.0 M solution of HCl in 1,4-dioxane (100 ml) was added to a solution of [1-(2-cyano-1-methyl-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (50.0 mmol) in 1,4-dioxane (50 ml) at 25° C. The reaction mixture was stirred at 45° C. for 3.5 h, then was cooled to 25° C. and concentrated under reduced pressure to afford crude 3-(4-amino-piperidin-1-yl)-butyronitrile (hydrochloride salt) as a beige solid. 1H NMR (400 MHz, DMSO) δ 8.52 (s, 2H), 4.21 (s, 2H), 3.83-3.68 (m, 1H), 3.49-3.25 (m, 2H), 3.17 (dd, J=16.9, 8.0 Hz, 1H), 2.23-1.99 (m, 2H), 1.42 (d, J=6.7 Hz, 1H). This material was used in the next step below without additional purification or characterization.

Workup

  1. temperaturewas cooled to 25° C.
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba7a64204e624686a150cf3d2a9156f6
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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