Benzoyl chloride → HCID 69418259, compound

HRID 456460Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][N:23]([C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

4-[2-(Piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (Preparation 49A) (311 mg, 0.86 mmol) was dissolved in CH2Cl2 (15 mL) under nitrogen and cooled to 0° C. Benzoyl chloride (0.3 mL, 2.58 mmol) was added followed by dropwise addition of triethylamine (0.48 mL, 3.44 mmol). The mixture was warmed to r.t. and stirred for about 16 hours. Methylene chloride (20 mL) was added, and the solution was washed with saturated NaHCO3 (20 mL)and brine (20 mL), and then dried over magnesium sulfate. The solvents were removed under reduced pressure, and the residue was purified by flash column chromatography on silica to afford the final compound as a white solid (330 mg, 83%).

Workup

temperatureThe mixture was warmed to r.t.
washthe solution was washed with saturated NaHCO3 (20 mL)and brine (20 mL)
dry with materialdried over magnesium sulfate
customThe solvents were removed under reduced pressure
customthe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record: ord-075bebf8c7374ce08cdfd7bfecbcd2cf
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186715B2

Reaction notes

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