Formaldehyde → HCID 14852998, compound

HRID 845054Notes

Reaction equation

HRID 845054 reaction equation
[Cl-:1].[CH3:2][NH2+:3][CH3:4].C=O.C(O[C:11](=[O:13])[CH3:12])(=O)C.[C:14]([NH:17][C:18]1[CH:19]=[C:20]2C(=[CH:25][CH:26]=1)[C:23](=O)[CH2:22][CH2:21]2)(=[O:16])[CH3:15]>Cl>[ClH:1].[C:14]([NH:17][C:18]1[CH:19]=[C:20]2[C:12](=[CH:25][CH:26]=1)[C:11](=[O:13])[CH:22]([CH2:23][N:3]([CH3:4])[CH3:2])[CH2:21]2)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 7918Acetic AnhydrideHCID 312894N-(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetamideHCID 12954980Dimethylazanium;chloride

Product 1

HCID 14852998HCID 14852998, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Conditions

Temperature
100 °C

Procedure

Dimethylammonium chloride (8.0 g), formalin solution (5.1 ml, 37%) and concentrated hydrochloric acid (2 drops) were stirred at room temperature for 5 minutes, then added to acetic anhydride (35 ml). After 20 minutes, vigorous boiling occurred. 5-Acetamido-indanone (11.5 g) was added and the mixture stirred at 100° C. for one hour, then concentrated. The crude product was treated with acetone (100 ml) for 3 minutes then the mixture was reconcentrated. Water (150 ml) was added and unreacted ketone was extracted from the mixture into dichloromethane. The aqueous layer was separated, basified with dimethylamine and shaken with dichloromethane (100 ml). The organic layer was removed, evaporated and the gummy residue obtained was partitioned between dilute hydrochloric acid and dichloromethane. The aqueous layer was separated and concentrated to low volume to give white feathery needles (7.6 g, m.p. 182°-183° C.) of 5-acetamido-2-dimethylaminomethyl-1-indanone hydrochloride.

Workup

  1. concentrationconcentrated
  2. additionThe crude product was treated with acetone (100 ml) for 3 minutes
  3. additionWater (150 ml) was added
  4. extractionunreacted ketone was extracted from the mixture into dichloromethane
  5. customThe aqueous layer was separated
  6. stirringshaken with dichloromethane (100 ml)
  7. customThe organic layer was removed
  8. customevaporated
  9. customthe gummy residue obtained
  10. customwas partitioned between dilute hydrochloric acid and dichloromethane
  11. customThe aqueous layer was separated
  12. concentrationconcentrated to low volume

Sources & evidence

ORD record
ord-4762aa7f6c9448a5b1dd55186226613f
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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