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

HRID 1387018
Notes
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Reaction equation

HRID 1387018 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 105125306-Methoxy-N,N-dimethylbenzo[b]thiophen-2-amine

Product 1

HCID 211827022-Dimethylamino-6-methoxybenzo[b]thiophen-3-yl 4-[(1-Pyrrolidinyl)methyl]phenyl KetoneYield 74%

Reagents, catalysts & solvents 1

HCID 7964Chlorobenzene
Solvent

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

  1. washAfter dilution with THF (20 mL), the mixture was washed with saturated aqueous NaHCO3 (5 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes