Acetic Acid → HCID 67045312, compound

HRID 1023687Notes

Reaction equation

HRID 1023687 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][CH:13]=1)[CH2:5]2.C=O.[C:23]([BH3-])#[N:24].[Na+].[C:27](O)(=O)C>C1COCC1.C(OCC)(=O)C>[CH3:27][N:24]([CH3:23])[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][CH:13]=1)[CH2:5]2

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67045281HCID 67045281, compound

Product 1

HCID 67045312HCID 67045312, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-amino-2-(4-propyl-phenyl)-isoindol-1-one (89 mg, 0.33 mmol) obtained in Example 2 and formalin (0.26 ml) in THF (5 ml) was added with 95% sodium cyanoborohydride (66 mg, 1.00 mmol) and acetic acid (0.1 ml), the mixture was stirred at room temperature for 30 minutes, and then further added with acetic acid (0.1 ml), and the mixture was stirred at room temperature for 7 hours. The reaction solution was added with ethyl acetate for extraction. The ethyl acetate layer was washed with 1 N aqueous potassium hydroxide and saturated brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform) and recrystallization (chloroform/n-hexane) to obtain 5-dimethylamino-2-(4-propyl-phenyl)-isoindol-1-one (Compound 1) as a pale yellow powdery substance (75.8 mg, yield: 77.1%).

Workup

  1. stirringthe mixture was stirred at room temperature for 7 hours
  2. washThe ethyl acetate layer was washed with 1 N aqueous potassium hydroxide and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform) and recrystallization (chloroform/n-hexane)

Sources & evidence

ORD record
ord-375a57b1069f46d98c88d382f71cb1d5
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Reaction notes

Loading…