4,4-Difluoropiperidine hydrochloride → HCID 25254842, compound

HRID 219459Notes

Reaction equation

HRID 219459 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])=[C:9]([O:23][CH3:24])[C:8]([Cl:25])=[C:7]([CH3:26])[C:6]=1[C:27](=[O:29])[CH3:28].Cl.[F:31][C:32]1([F:38])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[Cl:25][C:8]1[C:7]([CH3:26])=[C:6]([C:27](=[O:29])[CH3:28])[C:5]([O:4][CH2:3][CH2:2][N:35]2[CH2:36][CH2:37][C:32]([F:38])([F:31])[CH2:33][CH2:34]2)=[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]=1[O:23][CH3:24]

Participants

3

Reactant 2

HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 595835231-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Product 1

HCID 25254842HCID 25254842, compoundYield 31%

Procedure

Example 8a (56 mg, 0.12 mmol) was reacted with 4,4-difluoropiperidine hydrochloride (2.0 eq.) as described under General Procedure J to afford the title compound (19 mg, 31%) as a clear yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.05 (t, J=5.7 Hz, 2H), 3.97 (t, J=6.6 Hz, 2H), 3.84 (s, 3H), 3.11-2.89 (m, 1H), 2.66 (t, J=5.7 Hz, 2H), 2.58 (m, 4H), 2.49 (s, 3H), 2.18 (s, 3H), 2.05-1.92 (m, 6H), 1.30 (d, J=6.9 Hz, 3H). MS (ES+) m/z 528 (M+H+).

Sources & evidence

ORD record
ord-56abe7fac8c847ee9e776c95cf165f4e
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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