1-Chloro-4-(chloromethyl)benzene → 3-Carbamoyl-1-(4-chlorobenzyl)piperidine

HRID 133583

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1.[NH:17]1[CH2:25][CH2:24][CH2:23][CH:19]([C:20]([NH2:22])=[O:21])[CH2:18]1.C([O-])(O)=O.[Na+]>C(#N)C.C(O)C.O>[C:20]([CH:19]1[CH2:23][CH2:24][CH2:25][N:17]([CH2:13][C:12]2[CH:15]=[CH:16][C:9]([Cl:8])=[CH:10][CH:11]=2)[CH2:18]1)(=[O:21])[NH2:22]

Participants

Conditions

Temperature: 50 °C

Procedure

Triethylamine (7.0 mL, 50 mmol) and 4-chlorobenzyl chloride (8.05 g, 50 mmol) were added to a solution of nipecotamide (6.40 g, 50 mmol) in acetonitrile (150 mL) and ethanol (20 mL). The resulting reaction mixture was stirred at 50° C. for 16 hours and cooled to room temperature. A saturated aqueous solution of NaHCO3 (50 mL) and water (150 mL) were then added, and the resulting mixture was extracted with ethyl acetate (150 mL×3). The extracts were washed with brine, dried over Na2SO4 and concentrated to afford a light-red solid. The obtained crude solid was washed with ether (100 mL) to provide 3-carbamoyl-1-(4-chlorobenzyl)piperidine (6.98 g, 54%).

Workup

customThe resulting reaction mixture
temperaturecooled to room temperature
extractionthe resulting mixture was extracted with ethyl acetate (150 mL×3)
washThe extracts were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customto afford a light-red solid
customThe obtained crude solid
washwas washed with ether (100 mL)

Sources & evidence

ORD record: ord-6f4b2841fe374baeadbc5ec0cd15c8f0
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390830B1

Linked notes

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