ChemicalBook CAS DataBase List (4-CHLORO-BENZYL)-METHYL-AMINE

(4-CHLORO-BENZYL)-METHYL-AMINE synthesis

10synthesis methods

Product Name:(4-CHLORO-BENZYL)-METHYL-AMINE
CAS Number:104-11-0
Molecular formula:C8H10ClN
Molecular Weight:155.62

104-83-6 Synthesis

104-83-6
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$15.00/50g

74-89-5 Synthesis

74-89-5
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$13.44/25ML

104-11-0
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$22.00/1g

Yield: 81%

Reaction Conditions:

in tetrahydrofuran;water at 0 - 20;Inert atmosphere;

Steps:

(4-Chlorobenzyl)methyIamine (30)To a stirred solution of 4-chlorobenzylchloride (3.00 g, 18.63 mmol) in THF (300 ml) under N₂ at 0 ⁰C, was added methylamine solution in water (40% v/v) (9.03 mi, 93.48 mmol) and the reaction allowed to progress at room temperature overnight. The solvent was removed by rotary evaporation with water removed by azeotroping with toluene. The crude product was purified directly by column chromatography using EtOAc (100%) followed by EtOAc: MeOH: NEt₃ (92: 5: 3) as eluent to give 30 as a yellow oil (2.49 g, 81%); ¹H NMR (CDCi₃, 300 MHz) δ 7.25 - 7.18 (4H, m), 3.66 (2H, s), 2.38 (3H, s), 1.65 ( 1H, s); ¹³C NMR (CDCI₃, 100 MHz) δ 138.6 (IV), 132.6 (IV), 129.5 (2C), 128.4 (2C), 55.2, 35.8; HRMS (ESI): Found 156.0580 (M⁺). C₈H₁₀NCI (M⁺) requires 156.0556.

References:

UNIVERSITY OF CAPE TOWN;HUNTER, Roger;EGAN, Timothy John;ZISHIRI, Vincent Kudakwashe WO2010/18555, 2010, A2 Location in patent:Page/Page column 19; 23