4-Methylpiperidine → HCID 24853493, compound

HRID 641093Notes

Reaction equation

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

Participants

Reactant 2

HCID 693814-Methylpiperidine

HCID 59007792HCID 59007792, compound

Product 2

HCID 24853493HCID 24853493, compound

HCID 59007780HCID 59007780, compound

Procedure

In a stainless steel autoclave, 500 mg (1.4 mmol) of 3-(2-chloro-6-fluorophenyl)-2,4-dichloro-6-(pyrimidin-2-yl)pyridine (Example C) and 15 g of 4-methylpiperidin were heated at 140° C. for 12 h. The volatile components were removed under reduced pressure and the residue was chromatographed on silica gel using cyclohexane/ethyl acetate. It was possible to isolate 220 mg of 4-chloro-3-(2-chloro-6-fluorophenyl)-2-(4-methylpiperidinyl)-6-(pyrimidin-2-yl)pyridine (m.p. 129° C.) and 60 mg of 2-chloro-3-(2-chloro-6-fluorophenyl)-4-(4-methylpiperidinyl)-6-(pyrimidin-2-yl)pyridine (m.p. 129° C.).

Workup

customThe volatile components were removed under reduced pressure
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-47ab4f7d50844b2c9db4727e4913dfa8
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07695728B2

Reaction notes

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