Water → 2-Butyl-1-{1-[3-(4-fluorophenylsulfanyl)-propyl]-piperidin-4-yl}-1H-benzimidazole

HRID 2240283Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH2:13]([C:17]1[N:21]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:20]2[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=2[N:18]=1)[CH2:14][CH2:15][CH3:16].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:13]([C:17]1[N:21]([CH:22]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][S:5][C:6]3[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=3)[CH2:24][CH2:23]2)[C:20]2[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=2[N:18]=1)[CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 1-(3-bromopropylsulfanyl)-4-fluorobenzene (0.2 g) and 2-butyl-1-piperidin-4-yl-1H-benzimidazole (0.3 g) in DMF (5 ml) was added K2CO3 (0.6 g) and KI (0.05 g). The mixture was heated at 100° C. for 1 h, and then allowed to cool to rt. Water (50 ml) was added and the mixture extracted with ethyl acetate (80 ml), and the organic layer separated and washed with water. This was further dried and concentrated in vacuo. The oil was purified by flash chromatography (9:1 DCM:MeOH) to yield 0.3 g of the title compound as colourless crystals. Mp. 159-161° C.

Workup

temperatureto cool to rt
extractionthe mixture extracted with ethyl acetate (80 ml)
customthe organic layer separated
washwashed with water
customThis was further dried
concentrationconcentrated in vacuo
customThe oil was purified by flash chromatography (9:1 DCM:MeOH)

Sources & evidence

ORD record: ord-6c4e720a98f64b2d8cc2ebda8462f62d
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723360B2

Reaction notes

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