Formaldehyde → HCID 20568898, compound

HRID 1578110Notes

Reaction equation

HRID 1578110 reaction equation
C=O.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])[CH2:15][CH2:14]1.[C:30]([O-])(=O)C.[Na+]>C(O)(=O)C.O>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:30][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:20](=[O:29])[C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]3=[O:28])[CH2:15][CH2:14]2)=[CH:4]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 798IndoleHCID 517045Sodium AcetateHCID 218825602-(Piperidin-4-yl)isoindoline-1,3-dione hydrochloride

Product 1

HCID 20568898HCID 20568898, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Formaldehyde (0.84 cm3, 40% aq. w/v, 11.3 mmol) was added to a stirred and cooled mixture of indole (1.32 g, 11.3 mmol), 2-(piperid-4-yl)-1H-isoindol-1,3-(2H)-dione, hydrochloride (3.0 g, 11.3 mmol), and sodium acetate (0.93 g, 11.3 mmol) in glacial acetic acid (10 cm3). The suspension was stirred at room temperature for 5 hours, then poured into water and a gummy precipitate filtered off. The mother liquors were basified by addition of 0.880 ammonia to precipitate the title compound, which was collected and dried (2.52 g, 62.4%).

Workup

  1. temperaturecooled
  2. stirringThe suspension was stirred at room temperature for 5 hours
  3. filtrationa gummy precipitate filtered off
  4. additionThe mother liquors were basified by addition of 0.880 ammonia
  5. customto precipitate the title compound, which
  6. customwas collected
  7. customdried (2.52 g, 62.4%)

Sources & evidence

ORD record
ord-1eb450068dfb450db327d477248e24e9
Source dataset
uspto-grants-1981_09
Patent number
US04291042

Reaction notes

Loading…