Hydrochloric Acid → 4-(2-Chlorophenyl)-4-cyanopiperidine hydrochloride

HRID 895468Notes

Reaction equation

HRID 895468 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])([C:21]#[N:22])[CH2:17][CH2:16]1)=O)(C)(C)C>>[ClH:29].[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:18]1([C:21]#[N:22])[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 21712251Tert-butyl 4-(2-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Product 1

HCID 223792744-(2-Chlorophenyl)-4-cyanopiperidine hydrochlorideYield 200%

Procedure

A solution of HCl in dioxane (4M, 200 mL, 800 mmol) was added to the Boc-protected amine 18.15 (18.4 g, 57.4 mmol). After 1.5 h the solvent was evaporated and the residue dried in vacuo, giving 14.8 g (57.4 mmol, 100%) of 7.15, colorless solid, mp 241-243° C. (decomp.). 1H NMR (200 MHz, CDCl3): δ=2.5-2.8 (brm, 4H), 3.4-3.6 (brm, 2H), 3.6-3.8 (brm, 2H), 7.33-7.39 (m, 3H), 7.48-7.53 (m, 1H), 10.01 (brs, 2H). C12H14Cl2N2 (257.16): calcd. C 56.05, H 5.49, Cl 27.57, N 10.89; found C 55.67, H 5.48, Cl 27.86, N 10.61.

Workup

  1. customAfter 1.5 h the solvent was evaporated
  2. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-426cc35a1a644f22b325f017bcf4ff62
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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