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

HRID 1905719Notes

Reaction equation

HRID 1905719 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-0e3572c5b3ef4f7280071c967144d162
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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