Hydrochloric Acid → N-(2-cyanoethyl)-4-aminopiperidine

HRID 1257602Notes

Reaction equation

HRID 1257602 reaction equation
Cl.C(OC(=O)[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][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]([CH2:15][CH2:16][C:17]#[N:18])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59862765tert-Butyl 1-(2-cyanoethyl)piperidin-4-ylcarbamate

Product 1

HCID 22562162N-(2-cyanoethyl)-4-aminopiperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A 4.0 M solution of HCl in 1,4-dioxane (100 ml) was added to a solution of [1-(2-cyano-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 50° C. for 5 h, then was concentrated under reduced pressure to afford crude 3-(4-amino-piperidin-1-yl)-propionitrile (hydrochloride salt) as a white solid. 1H NMR (400 MHz, DMSO) δ 11.43 (s, 1H), 8.48 (s, 2H), 3.58-3.50 (m, 2H), 3.46-3.32 (m, 2H), 3.31-3.21 (m, 1H), 3.17 (t, J=7.2 Hz, 2H), 3.13-2.95 (m, 2H), 2.15 (d, J=13.5 Hz, 2H), 2.04-1.86 (m, 2H). This material was used in the next step below without additional purification or characterization.

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-d26b3596fb0449348619b58737d90ab3
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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