4'-Fluoroacetophenone → 1-(4-{4-[(1-Cyclobutyl-4-piperidinyl)methyl]-1-piperidinyl}phenyl)ethanone

HRID 1869642Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

1-Cyclobutyl-4-(4-piperidinylmethyl)piperidine (may be prepared as described in Description 6) (0.15 g), 4-fluoroacetophenone (0.133 g) and potassium carbonate (0.177 g) were dissolved in DMSO (2 ml) and heated at 120° C. for 7 min in the microwave reactor. The crude reaction mixture was passed through an SCX column (10 g, eluting with methanol [80 ml] then 2 N NH3 in methanol [80 ml]). Chromatography of the crude ketone (silica gel, eluting with methanol/dichloromethane, 0-25%) afforded the title compound (E25) (0.05 g). MS electrospray (+ion) 355 (MH+).

Workup

customThe crude reaction mixture
washeluting with methanol [80 ml]

Sources & evidence

ORD record: ord-2dc4eaaad3bc4d16b4b9fdb9c76216c5
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638631B2

Reaction notes

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