HCID 11668403, compound → HCID 11711073, compound

HRID 2427643Notes

Reaction equation

HRID 2427643 reaction equation
[CH3:1][N:2]([CH3:30])[CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=1)[CH2:9]2.[H][H]>C(O)C.[Pd]>[CH3:30][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:19][CH:18]=1)[CH2:9]2

Participants

5

Reactant 2

HCID 11668403HCID 11668403, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11711073HCID 11711073, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-(3-dimethylamino-prop-1-ynyl)-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.055 g, 0.14 mmol) in ethanol (25 mL) was treated with 10% palladium on carbon (15 mg). The mixture was shook vigorously under 45 p.s.i. hydrogen for 3 h. The resulting reaction mixture was filtered through Celite and the filtrate concentrated under reduced pressure. Silica gel column chromatography of the resulting material using 5:1 CHCl3-MeOH afforded 5-(3-dimethylamino-propyl)-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.051 g, 83%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.85 (m, 2H), 2.27 (s, 6H), 2.36 (t, 2H), 2.74 (t, 2H), 4.25 (s, 2H), 4.76 (s, 2H), 6.92-7.36 (m, 11H), 7.80 (d, 1H). GC-MS: 400 (M)+

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through Celite
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-f1a0730b64b44ea4918fff68227293cf
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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