Dimethylamine → HCID 20138881, compound

HRID 280146Notes

Reaction equation

HRID 280146 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=O)=[CH:5][CH:4]=1.[CH3:14][NH:15][CH3:16]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl.[Ti]>[CH3:14][N:15]([CH3:16])[C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][CH:9]=1

Participants

6

Reactant 2

HCID 674DimethylamineHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 20138881HCID 20138881, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 23963TitaniumCatalystHCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of titanium tetrachloride (53.8 g, 31.2 ml) in dry toluene (200 ml) is added over a period of 45 minutes to a stirred solution of 7-methoxy-1-tetralone (100.5 g) and dimethyl amine (171 g) in dry toluene (2 l) while maintaining a reaction temperature of ≤10° C. When the addition of the titanium is complete, the ice bath is removed and the solution allowed to reach RT. The solution is stirred at RT for 3 hours. The solids are filtered, washed with dry toluene and the filtrate evaporated in vacuo, yielding 101.4 g of an amber oil which is used in the next step without further treatment.

Workup

  1. temperaturewhile maintaining a reaction temperature of ≤10° C
  2. customthe ice bath is removed
  3. customto reach RT
  4. filtrationThe solids are filtered
  5. washwashed with dry toluene
  6. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-032e3c2be01c4129889814826fa7ebd1
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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