Hydrogen Peroxide → 4-((1-Benzylpiperidin-4-yl)oxy)benzamide

HRID 459927Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:24].[K+].[K+].OO>CS(C)=O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([NH2:20])=[O:24])=[CH:21][CH:22]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Combine 4-(1-benzyl-piperidin-4-yloxy)-benzonitrile (74 mg, 0.25 mmol), DMSO (2.5 mL) and powdered potassium carbonate (18 mg, 0.13 mmol). Cool the resulting mixture to 0° C. and add hydrogen peroxide (76 μL). After addition, stir the mixture at room temperature for 1 h. Quench the reaction mixture with water (2 mL). Filter the precipitate formed rinsing with diethyl ether to give the title compound (57 mg, 73%). Mass spectrum (ion spray): m/z=311.1 (M+1); 1H NMR (CDCl3): 7.79 (ad, J=8.6 Hz, 3H), 7.32–7.21 (m, 5H), 7.14 (bs, 1H), 6.95 (d, J=8.6 Hz, 2H), 4.49–4.42 (m, 1H), 3.31 (s, 2H), 2.69–2.62 (m, 2H), 2.27–2.19 (m, 2H), 1.96–1.89 (m, 2H), 1.66–1.56 (m, 2H).

Workup

additionAfter addition
customQuench the reaction mixture with water (2 mL)
filtrationFilter the precipitate
customformed
washrinsing with diethyl ether

Sources & evidence

ORD record: ord-1b2bf443c72643efadbbc39768442ec0
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196100B2

Reaction notes

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