Hydrochloric Acid → 1-[4-(3-Methyl-[1,2,4]oxadiazol-5-yl)-benzoyl]-4-phenyl-piperidine-4-carboxylic acid

HRID 2189981Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 1-[4-(3-methyl-[1,2,4]oxadiazol-5-yl)-benzoyl]-4-phenyl-piperidine-4-carboxylic acid methyl ester (156 mg, 0.385 mmol) in methanol (2 mL) was added an aqueous solution of KOH (3M, 770 μL, 2.31 mmol) and stirred at 65° C. for 12 h. The mixture was cooled to 0° C. and adjusted to pH=7 with 1N aqueous HCl. The solvent was evaporated under reduced pressure and the residue was co-evaporated with toluene to give 316 mg (purity ˜48%) 1-[4-(3-methyl-[1,2,4]oxadiazol-5-yl)-benzoyl]-4-phenyl-piperidine-4-carboxylic acid which was used directly for the next step. MS ISP (m/e): 392.2 [(M+H)+].

Workup

temperatureThe mixture was cooled to 0° C.
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-229c06e0a19d48f7a0f36205d91ec930
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324250B2

Reaction notes

Loading…