Morpholine → 1-[3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-2-methyl-6-(3-morpholin-4-yl-propoxy)-phenyl]-ethanone

HRID 219466Notes

Reaction equation

HRID 219466 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH3:16])=[C:10]([O:24][CH3:25])[C:9]([Cl:26])=[C:8]([CH3:27])[C:7]=1[C:28](=[O:30])[CH3:29].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[Cl:26][C:9]1[C:8]([CH3:27])=[C:7]([C:28](=[O:30])[CH3:29])[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[C:11]([O:12][CH2:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH3:16])[C:10]=1[O:24][CH3:25]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 595835011-{2-(3-Bromo-propoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Product 1

HCID 252546841-[3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-2-methyl-6-(3-morpholin-4-yl-propoxy)-phenyl]-ethanoneYield 88.6%

Procedure

Example 22a (40 mg, 0.08 mmol) was reacted with morpholine (0.2 mL, 2.29 mmol) as described under General Procedure G and the crude mixture was purified by flash chromatography (silica-gel, DCM/EtOAc/MeOH 1:0:0, 9:8:2) to afford the title compound (36 mg, 88%) as yellow/brown oil. 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.00 (t, J=6.4 Hz, 2H), 3.94 (t, J=6.7 Hz, 2H), 3.83 (s, 3H), 3.72-3.69 (m, 4H), 3.07-2.95 (m, 1H), 2.46 (s, 3H), 2.45-2.40 (m, 6H), 2.18 (s, 3H), 2.02-1.99 (m, 2H), 1.88-1.79 (m, 2H), 1.30 (d, J=6.9 Hz, 3H). MS (ES+) m/z 508.3 (M+H+)

Workup

  1. customthe crude mixture was purified by flash chromatography (silica-gel, DCM/EtOAc/MeOH 1:0:0, 9:8:2)

Sources & evidence

ORD record
ord-c06daa4484074ea9a4ac1759fedca1b1
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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