Water → 1-{1-[3-(4-Fluorophenoxy)-propyl]-piperidin-4-yl}-1H-benzimidazole

HRID 2240286Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH2:3][CH2:2]1.Cl[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][CH2:18][CH2:17][N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=[CH:8]3)[CH2:5][CH2:6]2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 1-piperidin-4-yl-1H-benzimidazole (4.02 g) and 1-(3-chloropropoxy)-4-fluorobenzene (4.16 g) in DMF (50 ml) was added K2CO3 (4.1 g) and KI (0.2 g). The mixture was heated at 90° C. for 2 h, and then allowed to cool to rt. Water (100 ml) was added and the mixture extracted with ethyl acetate (2×80 ml), and the organic layer separated and washed with water. This was further dried and concentrated in vacuo. The free base converted to the hydrochloride salt by action of HCl in ethanol. The solid was recrystallised from ethanol-diethylether to yield 4.7 g of the title compound as colourless crystals. MP. 233-235° C.

Workup

temperatureto cool to rt
extractionthe mixture extracted with ethyl acetate (2×80 ml)
customthe organic layer separated
washwashed with water
customThis was further dried
concentrationconcentrated in vacuo
customThe solid was recrystallised from ethanol-diethylether

Sources & evidence

ORD record: ord-47748616543947818459e986b8a4938c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723360B2

Reaction notes

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