Ethyl Acetate → HCID 21182612, compound

HRID 1386975Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[C:18]4[CH:33]=[CH:32][CH:31]=[CH:30][C:19]=4[S:20][C:21]=3[C:22]3[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=3)=[O:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.N1C=CC=CC=1.CCOC(C)=O>O>[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([C:17]3[C:18]4[CH:33]=[CH:32][CH:31]=[CH:30][C:19]=4[S:20][C:21]=3[C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)=[O:16])=[CH:13][CH:14]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 160 °C

Procedure

A 100 mL round bottom flask containing 300 mg (0.66 mmol) of 2-(4-methoxyphenyl)benzo[b]thiophen-3-yl 4-[3-(1-pyrrolidinyl)propyl]phenyl ketone (Part A) was filled with 20 g of pyridine hydrochloride. The flask was heated to 160° C. to melt the solid. After 16 h, the reaction was cooled to warm temperature, diluted with 50 mL of H2O, and transferred to separatory funnel containing 50 mL H2O and 50 mL of EtOAc. The two layers were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The combined EtOAc layers were dried over Na2SO4 and concentrated in vacuo to give 325 mg of a yellow oil. Purification by radial chromatography (SiO2; gradient of 2-10% MeOH in CH2Cl2) afforded 200 mg (0.45 mmol; 69%) of the title compound as a viscous yellow oil.

Workup

temperaturethe reaction was cooled
temperatureto warm temperature
customtransferred to separatory funnel
customThe two layers were separated
extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
dry with materialThe combined EtOAc layers were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0b43bfb94eaf4dc6b59c272f7af0b190
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265575B1

Reaction notes

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