Potassium Carbonate → 4-(4-Ethoxymethyl-5-phenyl-oxazol-2-yl)-1-[2-(4-methoxy-phenyl)-ethyl]-piperidine

HRID 2288994Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.Cl.[CH2:13]([O:15][CH2:16][C:17]1[N:18]=[C:19]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[O:20][C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:14].C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>C(O)C>[CH2:13]([O:15][CH2:16][C:17]1[N:18]=[C:19]([CH:28]2[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=3)[CH2:30][CH2:29]2)[O:20][C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:14]

Participants

Conditions

Temperature: 150 °C

Procedure

1-(2-chloroethyl)-4-methoxybenzene (486 mg, 2.8 mmol), 4-(4-ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidine hydrochloride (1 g, 2.2 mmol), prepared as in Intermediate 4, K2CO3 (393 mg, 2.85 mmol) and Nal (427 mg, 2.85 mmol) in ethanol are mixed together in a sealed tube and heated to 150° C. overnight. The mixture is cooled, filtered and concentrated. The crude material is purified by column chromatography (SiO2, 10% methanol: methylene chloride), followed by another column (SiO2, 15% methanol: ethyl acetate) to afford an oil which is triturated from 70% hexane; ether, 800 mg of the title compound is obtained.

Workup

additionare mixed together in a sealed tube
temperatureThe mixture is cooled
filtrationfiltered
concentrationconcentrated
customThe crude material is purified by column chromatography (SiO2, 10% methanol: methylene chloride)
customto afford an oil which
customis triturated from 70% hexane

Sources & evidence

ORD record: ord-e14e7bb0a25a4878acbc1d2e69e60f44
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090825

Reaction notes

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