Pyrrolidine → 2-Dimethylamino-6-methoxybenzo[b]thiophen-3-yl 4-[(1-Pyrrolidinyl)methyl]phenyl Ketone

HRID 1387018Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH3:12][N:13]([CH3:25])[C:14]1[S:18][C:17]2[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:16]=2[CH:15]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>ClC1C=CC=CC=1>[N:26]1([CH2:2][C:3]2[CH:11]=[CH:10][C:6]([C:7]([C:15]3[C:16]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:17]=4[S:18][C:14]=3[N:13]([CH3:25])[CH3:12])=[O:8])=[CH:5][CH:4]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 0 °C

Procedure

4-(Chloromethyl)benzoyl chloride (105 mg, 0.558 mmol) was added to a stirred solution of 2-dimethylamino-6-methoxybenzo[b]thiophene (105 mg, 0.507 mmol) in chlorobenzene (1 mL) under nitrogen. The resultant mixture was heated in an oil bath at 110° C. for 2.5 h. The mixture was cooled to 0° C., treated with pyrrolidine (5 mL), then allowed to stir at room temperature for 2 h. After dilution with THF (20 mL), the mixture was washed with saturated aqueous NaHCO3 (5 mL). The organic layer was dried over MgSO4, filtered, concentrated, and chromatographed on silica [gradient 20-40% EtOAc in hexanes, then 0-10% EtOH/Et3N (2/1) in THF/hexanes (1/1)] to give 148 mg (74%) of the ketone as a foam.

Workup

washAfter dilution with THF (20 mL), the mixture was washed with saturated aqueous NaHCO3 (5 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customchromatographed on silica [gradient 20-40% EtOAc in hexanes

Sources & evidence

ORD record: ord-01d69db52bdf454d9401912001aada42
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265575B1

Reaction notes

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