Hydrochloric Acid → N,N-dimethyl-1-(4-nitrophenyl)piperidin-4-amine

HRID 1348563

Reaction equation

Cl.Cl.[CH3:3][N:4]([CH3:11])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.Cl>CO>[CH3:3][N:4]([CH3:11])[CH:5]1[CH2:10][CH2:9][N:8]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH2:7][CH2:6]1

Participants

Conditions

Temperature: 90 °C

Procedure

Dimethyl-piperidin-4-yl-amine dihydrochloride (Aldrich, 2.0 g, 9.95 mmol) and 4-fluoro-nitrobenzene (Aldrich, 2.5 g, 17.7 mmol) were added to methanol (30 mL). The mixture was heated to 90° C. and stirred for 3.5 hours. The mixture was treated with 1 N HCl to pH=1 and then extracted with diethyl ether (2×10 mL). The aqueous layer was treated with saturated sodium carbonate to pH=10 and then extracted with methylene chloride (2×20 mL). The organic layer was dried with sodium sulfate and the solvent was removed to give the desired product. 1.25 g, 50%. MS (m+H)+: 250.

Workup

extractionextracted with diethyl ether (2×10 mL)
additionThe aqueous layer was treated with saturated sodium carbonate to pH=10
extractionextracted with methylene chloride (2×20 mL)
dry with materialThe organic layer was dried with sodium sulfate
customthe solvent was removed

Sources & evidence

ORD record: ord-7a4df0aa5ce14d80a59cf2829f16ebe3
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211576B2

Linked notes

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