Water → 1-[(2-chloro-1H-indol-1-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1896438Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.Cl[CH2:14][N:15]1[CH2:19][CH:18]([CH2:20][CH2:21][CH3:22])[CH2:17][C:16]1=[O:23].O>CN(C=O)C>[Cl:3][C:4]1[N:5]([CH2:14][N:15]2[CH2:19][CH:18]([CH2:20][CH2:21][CH3:22])[CH2:17][C:16]2=[O:23])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

Conditions

Temperature: -20 °C

Procedure

At −78° C., NaH (60% in mineral oil; 220 mg, 5.52 mmol, 1.1 eq) is added to a solution of 2-chloro-1H-indole x160 (0.76 g, 5.02 mmol, 1 eq) in dry DMF (50 ml). The temperature is raised to −20° C. during 20 minutes, then 1-(chloromethyl)-4-propylpyrrolidin-2-one x63 (0.76 g, 5.02 mmol, 1 eq) dissolved in DMF (10 ml) is added drop wise. After 2 hours at room temperature, water (50 ml) is added. The aqueous layer is extracted with CH2Cl2 (3×30 ml). The combined organic layers are dried on anhydrous MgSO4, filtered off and concentrated under reduced pressure to obtain a liquid that is purified on silicagel (AcOEt/Benzine 1/9) yielding 1-[(2-chloro-1H-indol-1-yl)methyl]-4-propylpyrrolidin-2-one 274 as a colorless liquid (605 mg).

Workup

additionis added drop wise
extractionThe aqueous layer is extracted with CH2Cl2 (3×30 ml)
dry with materialThe combined organic layers are dried on anhydrous MgSO4
filtrationfiltered off
concentrationconcentrated under reduced pressure
customto obtain a liquid that
customis purified on silicagel (AcOEt/Benzine 1/9)

Sources & evidence

ORD record: ord-50e497455e474c4a9f487850217bb754
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518943B2

Reaction notes

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