Formaldehyde → 1(2H)-Naphthalenone, 2-((dimethylamino)methyl)-3,4-dihydro-, hydrochloride (1:1)

HRID 1021069Notes

Reaction equation

HRID 1021069 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[CH2:12]=O.[ClH:14].[CH3:15][NH:16][CH3:17]>>[ClH:14].[CH3:15][N:16]([CH2:12][CH:11]1[CH2:1][CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:9]1=[O:10])[CH3:17]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 107241-Tetralone

Product 1

HCID 1998671(2H)-Naphthalenone, 2-((dimethylamino)methyl)-3,4-dihydro-, hydrochloride (1:1)Yield 11%

Conditions

Temperature
25 °C

Procedure

Specifically, first, a mixture liquid was obtained by feeding 73 g (0.5 mol) of α-tetralone, 47.3 g (0.55 mol) of a 37% by mass aqueous formalin solution, and 45 g (0.55 mol) of dimethylamine hydrochloride to a 500-ml three-necked flask. Next, a bulb condenser was set to the three-necked flask, and then the inside atmosphere of the three-necked flask was replaced with nitrogen. Thereafter, the three-necked flask was immersed in an oil bath of 100° C., and the mixture liquid was stirred for 60 minutes with heating. After thus stirred, the mixture liquid was cooled with ice to 25° C., and was washed twice with diethyl ether (twice with 30 ml each). Subsequently, the thus washed mixture liquid was allowed to stand one day and one night (24 hours). White crystals formed in the mixture liquid were separated by filtration, and washed with acetone. The thus obtained white crystals were vacuum dried. Thus, 12.9 g of N,N-dimethylaminomethyl-1-tetralone hydrochloride was obtained (yield: 11%). Note that the thus obtained compound was subjected to NMR measurement. As a result, it was found that a purity of N,N-dimethylaminomethyl-1-tetralone hydrochloride was 85.7%, and that 14.3% of dimethylamine hydrochloride was included as a by-product.

Workup

  1. customSpecifically, first, a mixture liquid was obtained
  2. customNext, a bulb condenser was set to the three-necked flask
  3. customThereafter, the three-necked flask was immersed in an oil bath of 100° C.
  4. temperaturewith heating
  5. stirringAfter thus stirred
  6. washwas washed twice with diethyl ether (twice with 30 ml each)
  7. waitto stand one day and one night
  8. custom(24 hours)
  9. customWhite crystals formed in the mixture liquid
  10. customwere separated by filtration
  11. washwashed with acetone
  12. customdried

Sources & evidence

ORD record
ord-f22836ff09f0471997db7b6838956b2c
Source dataset
uspto-grants-2014_05
Patent number
US08716531B2

Reaction notes

Loading…