Sodium Bicarbonate → 3-isopropenyl-1-{2-[4-((5-fluoro-3-indolyl)methyl)piperidino]ethyl}-2H-benzimidazol-2-one

HRID 1196614Notes

Reaction equation

C(N1C2C([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([CH2:21][C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=5)[NH:24][CH:23]=4)[CH2:17][CH2:16]3)=CC=CC=2NC1=O)(C)=C.[C:33]([N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38](CCCl)[C:37]1=[O:48])([CH3:35])=[CH2:34].FC1C=C2C(=CC=1)NC=C2CC1CCNCC1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1>[C:33]([N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=4)[NH:24][CH:23]=3)[CH2:19][CH2:20]2)[C:37]1=[O:48])([CH3:35])=[CH2:34]

Participants

Conditions

Temperature: 20 °C

Procedure

3-Isopropenyl-{2-[4-((5-fluoro-3-indolyl)methyl)piperidino]ethyl}-2H-benzimidazolin-2-one may be prepared in the following manner: the procedure is as in Example 25, starting with 3-isopropenyl-1-(2-chloroethyl)-2H-benzimidazolin-2-one (2.4 g), 4-[(5-fluoro-3-indolyl)methyl]piperidine (2.3 g) and sodium bicarbonate (0.8 g) in a mixture of dimethylformamide (40 cc) and tetrahydrofuran (20 cc). The mixture is heated to boiling for 10 hours and then cooled to a temperature in the region of 20° C. After purification by flash chromatography on a silica column under a stream of nitrogen and moderate pressure (0.5-1.5 bar) with dichloromethane and ethyl acetate as eluents, 3-isopropenyl-1-{2-[4-((5-fluoro-3-indolyl)methyl)piperidino]ethyl}-2H-benzimidazolin-2-one (3 g), m.p. 132° C., is obtained.

Workup

temperatureThe mixture is heated
customAfter purification by flash chromatography on a silica column under a stream of nitrogen and moderate pressure (0.5-1.5 bar) with dichloromethane and ethyl acetate as eluents

Sources & evidence

ORD record: ord-bdf86b03450846828bcddfd18f5f0879
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05114949

Reaction notes

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