Potassium Carbonate → 4-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}butyric acid methyl ester

HRID 1097289Notes

Reaction equation

HRID 1097289 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C([O-])([O-])=O.[K+].[K+].I[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:33](=[O:34])[CH:32]2[CH:27]([CH:28]=[CH:29][CH:30]=[CH:31]2)[C:26]1=[O:35]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[C:33](=[O:34])[CH:32]3[CH:27]([CH:28]=[CH:29][CH:30]=[CH:31]3)[C:26]2=[O:35])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21462751Methyl 4-(piperidin-4-yl)butanoateHCID 668110452-(4-Iodobutyl)-3a,7a-dihydroisoindole-1,3-dione

Product 1

HCID 668112194-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}butyric acid methyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2 (1.96 g, 8.86 mmol), K2CO3 (2.82 g, 17.72 mmol) and acetone (100 mL) was added 2-(4-iodobutyl)-3a,7a-dihydroisoindole-1,3-dione (2.93 g, 8.86 mmol). The newly formed suspension was stirred at ambient temperature for 48 hours. The solid was vacuum filtered and the filtrate was concentrated under vacuum. The resulting residue was subjected to column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the desired product 3 (0.63 g, 40%) as a white solid: 1H NMR (500 MHz; CDCl3) δ 1.16-1.28 (m, 3H), 1.65 (m, 2H), 1.60-1.72 (m, 4H), 1.86 (m, 2H), 2.26 (t, 2H), 2.32 (t, 2H), 2.88 (d, 2H) 3.64 (s, 3H), 3.70 (t, 2H), 7.68 (d, 2H), 7.72 (d, 2H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under vacuum
  3. washeluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bd9a0a83445a4034b9c4bff40b2be306
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

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