Chloroform methanol → 7-Chloro-5-[3-(4-methyl-piperazin-1-yl)-propyl]-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427668Notes

Reaction equation

HRID 2427668 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:23]#[C:24][CH2:25][N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[CH2:7]2.[H][H].C(Cl)(Cl)Cl.CO>C(O)C.[C].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:21])([F:20])[F:22])=[CH:17][CH:18]=1)[CH2:7]2

Participants

6

Reactant 3

HCID 21584188Chloroform methanolHCID 579493907-Chloro-5-[3-(4-methyl-piperazin-1-yl)-prop-1 ynyl)-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 579498057-Chloro-5-[3-(4-methyl-piperazin-1-yl)-propyl]-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-oneYield 30%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-chloro-5-[3-(4-methyl-piperazin-1-yl)-prop-1-ynyl)-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.125 g, 0.27 mmol) and 10% palladium-carbon (0.015 g) in ethanol (25 mL) was reduced under 45 p.s.i. hydrogen. Workup and silica gel column chromatography using 5:1 CHCl3-MeOH afforded 7-chloro-5-[3-(4-methyl-piperazin-1-yl)-propyl]-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.034 g, 30%). 1H NMR (300 MHz, CDCl3): 5 (ppm) 1.79 (m, 2H), 2.23-2.60 (m, 13H), 2.64 (t, 2H), 4.18 (s, 2H), 4.80 (s, 2H), 7.08 (s, 1H), 7.24 (s, 1H), 7.42 (d, 2H), 7.59 (d, 2H).

Sources & evidence

ORD record
ord-e9054e577df34d7b925f7d1ae6a6ced9
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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