HCID 19363234, compound → HCID 19363240, compound

HRID 850507Notes

Reaction equation

HRID 850507 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:16]=3[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:11]2=[O:31])=[CH:4][CH:3]=1.CO.[ClH:34]>CO>[ClH:34].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:16]=3[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:11]2=[O:31])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 19363234HCID 19363234, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 19363240HCID 19363240, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[2-(4-Aminophenyl)ethyl]-4,5-bispentyloxy-2,3-dihydroisoindol-1-one (22.37 g, 52.7 mmol, 1.0 eq) obtained in Example 7-34 was dissolved in methanol (100 ml), and 10% HCl- methanol solution (86.0 g, 236 mmol, 4.4 eq) was added to this solution. The mixture was stired at room temperature for 30 minutes, and concentrated under reduced pressure to remove the solvent. The obtained residue was washed with hexane and dissolved in ethanol by heating. After cooling at room temperature for 1 hour, the mixture was stirred under ice-cooling. The precipitated crystals were collected by filtration, washed with cold ethanol and dried in vacuo at 40° C. overnight to give 2-[2-(4-aminophenyl)ethyl]-4,5-bispentyloxy-2,3-dihydroisoindol-1-one hydrochloride (17.451 g, 72%) as colorless needles.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the solvent
  3. washThe obtained residue was washed with hexane
  4. dissolutiondissolved in ethanol
  5. temperatureby heating
  6. temperaturecooling
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed with cold ethanol
  9. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-bf521fb7f4c74ebbbbe7836bb4bf4fdf
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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