Acrylonitrile → tert-Butyl 1-(2-cyanoethyl)piperidin-4-ylcarbamate

HRID 1257601Notes

Reaction equation

[C:1](#[N:4])[CH:2]=[CH2:3].[C:5]([O:9][C:10](=[O:18])[NH:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6]>C(N(CC)CC)C.C(O)C>[C:5]([O:9][C:10](=[O:18])[NH:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:3][CH2:2][C:1]#[N:4])[CH2:14][CH2:13]1)([CH3:8])([CH3:6])[CH3:7]

Participants

Conditions

Temperature: 25 °C

Procedure

Acrylonitrile (3.6 ml, 55.0 mmol) and triethylamine (2 drops) were added sequentially to a solution of piperidin-4-yl-carbamic acid tert-butyl ester (10 g, 50.0 mmol) in ethanol (100 ml) at 25° C. The reaction mixture was stirred at 25° C. for 3.5 h, then was concentrated under reduced pressure to afford crude [1-(2-cyano-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester as a white solid. TLC: 5% CH3OH in CH2Cl2, Rf=0.56; 1H NMR (400 MHz, CDCl3) δ 4.42 (s, 1H), 3.45 (s, 1H), 2.82 (d, J=11.8 Hz, 2H), 2.67 (t, J=7.0 Hz, 2H), 2.49 (t, J=7.0 Hz, 2H), 2.18 (td, J=11.5, 2.3 Hz, 2H), 1.94 (d, J=12.1 Hz, 3H), 1.51-1.36 (m, 1H), 1.44 (s, 9H). This material was used in the next step below without additional purification or characterization.

Workup

concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-d7ee861af91541c2ae02c915740ebc7b
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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