Dimethylamine → 1-Dimethylamino-7-(3-phthalimido)propoxy-3,4-dihydronaphthalene

HRID 280143Notes

Reaction equation

HRID 280143 reaction equation
[C:1]1(=[O:26])[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][C:17]3=O)=[CH:12][CH:11]=2)[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.[CH3:27][NH:28][CH3:29]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:27][N:28]([CH3:29])[C:17]1[C:18]2[C:13](=[CH:12][CH:11]=[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:5]3[C:4](=[O:21])[C:3]4=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]4[C:1]3=[O:26])[CH:19]=2)[CH2:14][CH2:15][CH:16]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 135194987-(3-Phthalimidopropoxy)-tetralone

Product 1

HCID 137990101-Dimethylamino-7-(3-phthalimido)propoxy-3,4-dihydronaphthalene

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
1 °C

Procedure

A solution of titanium tetrachloride (5.4 g) in toluene (20 ml) is added over a period of 15 minutes to a stirred solution of 7-(3-phthalimido)propoxy-1-tetralone (19.9 g) suspended in a solution of anhydrous dimethyl amine (22 g) in dry toluene (200 ml) while maintaining a reaction temperature of about 1° C. under a N2 atmosphere. When the addition is complete, the reaction mixture is allowed to warm to RT and stirred at RT for 41/2 hours. The reaction mixture is filtered, the salts washed with dry toluene and the clear filtrate evaporated, affording a light yellow oil, which is stored under N2 and used in the next step without any further treatment.

Workup

  1. additionWhen the addition
  2. temperatureto warm to RT
  3. filtrationThe reaction mixture is filtered
  4. washthe salts washed with dry toluene
  5. customthe clear filtrate evaporated
  6. customaffording a light yellow oil, which

Sources & evidence

ORD record
ord-c39ea35a31224babb29743afb4ef58ed
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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