2-[(propylamino)methyl]phenol synthesis

6synthesis methods

Product Name:2-[(propylamino)methyl]phenol
CAS Number:84672-90-2
Molecular formula:C10H15NO
Molecular Weight:165.23

107-10-8
354 suppliers
$10.00/20mg

90-02-8 Synthesis

90-02-8
445 suppliers
$9.00/1g

84672-90-2
13 suppliers
$45.00/25mg

Yield:84672-90-2 55%

Reaction Conditions:

Stage #1: propylamine;salicylaldehyde in methanol at 0 - 20; for 3.5 h;
Stage #2: with sodium tetrahydroborate in methanol at 0 - 20;

Steps:

N-(Substituted benzyl) propan-1-amine (1a-o)

General procedure: The appropriate benzaldehydes (3.33 mmol) was dissolved in anhydrous methanol (20 ml) and cooled to 0 °C under stirring. To this cold mixture of n-propylamine (0.39 ml, 6.66 mmol) was added dropwise and stirring was continued for 30 min at 0 °C, then for 3 hr at ambient temp. The reaction mixture was again cooled to 0 °C and NaBH₄ (0.19 g, 5.0 mmol) was added in three portions at 10 min intervals. Then it was stirred at room temp for another 1 hr and the solvent was distilled to 1/3 of its original volume under vacuum. Cold water (5 ml) and NaHCO₃ (0.28 g, 3.33 mmol) were added to the above concentrated solution, stirred for 10 min and extracted with methylene chloride (3 x 20 ml). Combined organic phases was dried over Na₂SO₄ and evaporated the solvent and dried under vacuum to get the compounds (1a-o).

References:

Srivastav, Maneesh Kumar;Rajeeva;Salahuddin, Md.;Srinivasulu;Shanta Kumar [Indian Journal of Heterocyclic Chemistry,2014,vol. 24,# 2,p. 115 - 118]