Hydrochloric Acid → 1-Benzyl-4-(dimethylamino)piperidine-4-carbonitrile

HRID 453878Notes

Reaction equation

Cl.[CH3:2][NH:3][CH3:4].[C-]#N.[K+].[CH3:8][NH:9]C.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O.CO.C(OCC)(=O)C.CCOC(C)=O.CCCCCC>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]([N:3]([CH3:4])[CH3:2])([C:8]#[N:9])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

208 g (3 eq.) N,N-dimethylamine hydrochloride, 154 g (3 eq.) potassium cyanide in 154 ml water and 1050 ml (7 eq.) of a 40% dimethylamine solution were added to a solution of 150 g (1 eq.) 1-benzylpiperidin-4-one in 300 ml methanol and the mixture was cooled to 0° C. 75 ml (0.5 eq.) concentrated hydrochloric acid were then added at 0° C. and the reaction mixture was stirred for 24 h at room temperature. The reaction course was monitored by thin-layer chromatography (20% EtOAc/hexane). Once the conversion was complete, the solid that had formed was filtered out and washed with iced water (4 l). The solid obtained was then dissolved in ethyl acetate and dried with Na2SO4. Following removal of the solvent under reduced pressure, 165 g (85%) of crude product were obtained in the form of a solid.

Workup

customthe solid that had formed
filtrationwas filtered out
washwashed with iced water (4 l)
customThe solid obtained
dry with materialdried with Na2SO4
customremoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-71c4587b6e154fcabce253f94ad4d974
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492559B2

Reaction notes

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