Formaldehyde → HCID 22104533, compound

HRID 1457316Notes

Reaction equation

HRID 1457316 reaction equation
[CH2:1]=O.[ClH:3].[CH3:4][NH:5][CH3:6].[CH3:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[CH3:18])[C:14](=[O:19])[CH2:13][CH2:12][CH2:11]2>C(OC(=O)C)(=O)C>[ClH:3].[CH3:4][N:5]([CH2:1][CH:13]1[CH2:12][CH2:11][C:10]2[C:15](=[CH:16][C:17]([CH3:18])=[C:8]([CH3:7])[CH:9]=2)[C:14]1=[O:19])[CH3:6]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 3084576,7-Dimethyl-1-tetralone

Product 1

HCID 22104533HCID 22104533, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 37% formalin (18 g) and dimethylamine hydrochloride (18 g) was stirred at 25° C. for 30 minutes, and stirred at 70° C. for 30 minutes. The reaction temperature was raised to 80° C., and to the mixture was added dropwise acetic anhydride (80 ml). The reaction mixture was stirred at 80° C. for one hour, and thereto was added 3,4-dihydro-6,7-dimethyl-1(2H)-naphthalenone (26 g). The reaction temperature was raised to 90° C., and the mixture was stirred for 6 hours. The mixture was concentrated under reduced pressure to remove the solvent, and to the residue was added acetone. The precipitated crystals were collected by filtration, and washed with acetone to give 2-dimethylaminomethyl-3,4-dihydro-6,7-dimethyl-1(2H)-naphthalenone hydrochloride (39 g).

Workup

  1. stirringstirred at 70° C. for 30 minutes
  2. temperatureThe reaction temperature was raised to 80° C.
  3. stirringThe reaction mixture was stirred at 80° C. for one hour
  4. temperatureThe reaction temperature was raised to 90° C.
  5. stirringthe mixture was stirred for 6 hours
  6. concentrationThe mixture was concentrated under reduced pressure
  7. customto remove the solvent
  8. additionto the residue was added acetone
  9. filtrationThe precipitated crystals were collected by filtration
  10. washwashed with acetone

Sources & evidence

ORD record
ord-6d5194a465c44d06a1f138c9867fb16d
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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