1-Tetralone → HCID 20388034, compound

HRID 427104Notes

Reaction equation

HRID 427104 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6]Cl)[CH3:3].[Mg].[CH2:9]1[CH2:19][C:17](=O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1>O1CCCC1>[CH3:1][N:2]([CH3:3])[CH:4]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17][CH2:19][CH:9]=1)[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 107241-TetraloneHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 5462224Magnesium

Product 1

HCID 20388034HCID 20388034, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The Grignard reagent from 300 g (2.5 moles) of dimethylaminopropyl chloride and 60 g (2.5 moles) of magnesium turnings is prepared in 2 l. of tetrahydrofuran. To this is added 300 g (2.0 moles) of α-tetralone in 1 l. of tetrahydrofuran, at a rate to maintain reflux. After the addition the reflux is continued for 1.5 hours, then the mixture is cooled in ice and quenched with 500 ml of saturated ammonium chloride. The layers are separated, and the aqueous diluted with water and reextracted with ether. The organics are evaporated, then treated with a mixture of 350 ml of concentrated HCl and 1400 ml of glacial acetic acid at reflux for 1/2 hour. The solvents are removed in vacuo, and the residue taken up in water, and the aqueous extracted with benzene. Basification liberates the product which is extracted with benzene, dried over carbonate, the solvent evaporated, and the product distilled at 129° C., 0.3 mmHg to give 250 g (58%) of a light yellow liquid, 1-dimethylaminopropyl-3,4-dihydronaphthalene.

Workup

  1. temperaturereflux
  2. additionAfter the addition the reflux
  3. temperaturethe mixture is cooled in ice
  4. customquenched with 500 ml of saturated ammonium chloride
  5. customThe layers are separated
  6. additionthe aqueous diluted with water
  7. customThe organics are evaporated
  8. additiontreated with a mixture of 350 ml of concentrated HCl and 1400 ml of glacial acetic acid
  9. temperatureat reflux for 1/2 hour
  10. customThe solvents are removed in vacuo
  11. extractionthe aqueous extracted with benzene
  12. extractionis extracted with benzene
  13. dry with materialdried over carbonate
  14. customthe solvent evaporated
  15. distillationthe product distilled at 129° C.

Sources & evidence

ORD record
ord-07143d8ecfdb40b7802d297bda1f9d73
Source dataset
uspto-grants-1979_10
Patent number
US04172945

Reaction notes

Loading…