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

HRID 1500330Notes

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 off and washed with iced water (4 I). 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 off
washwashed with iced water (4 I)
customThe solid obtained
dry with materialdried with Na2SO4
customremoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-29fd339d2a16486ca24e88846996d948
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206156B2

Reaction notes

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