Hydrochloric Acid → HCID 68559292, compound

HRID 1804850Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14](N(OC)C)=[O:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:20][CH3:21].[CH2:22]([Mg]Br)[CH3:23].Cl>CCOCC.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([C:14](=[O:15])[CH2:22][CH3:23])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:20][CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-(4-chloro-3-methoxyphenyl)-N-methoxy-N-methylpiperidine-4-carboxamide (450 mg, 1.439 mmol) in anhydrous Et2O (10 mL) and THF (5 mL) was placed under nitrogen and cooled to −78° C. The solution was treated with ethylmagnesium bromide (2.16 mL of a 2.0 M solution in Et2O, 4.32 mmol) within 2 minutes and the stirred at for 20 minutes before warming the reaction to 0° C. The reaction was continued at 0° C. for 30 min and then poured into 0.5 M HCl (15 mL) and stirred vigorously for 5 min. The mixture was adjusted to pH 6 and extracted with Et2O. The extract was washed with brine, dried (MgSO4) and concentrated on a rotary evaporator to give 1-(1-(4-chloro-3-methoxyphenyl)piperidin-4-yl)propan-1-one (375 mg, 1.331 mmol, 93% yield) as a white solid.

Workup

temperaturebefore warming
customthe reaction to 0° C
waitThe reaction was continued at 0° C. for 30 min
stirringstirred vigorously for 5 min
extractionextracted with Et2O
washThe extract was washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-71448b041cdc4ed299ef60baab848593
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354432B2

Reaction notes

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