ChemicalBook CAS DataBase List 4-(4-FLUOROBENZYL)MORPHOLINE

4-(4-FLUOROBENZYL)MORPHOLINE synthesis

10synthesis methods

Product Name:4-(4-FLUOROBENZYL)MORPHOLINE
CAS Number:90754-65-7
Molecular formula:C11H14FNO
Molecular Weight:195.23

4394-85-8 Synthesis

4394-85-8
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$6.00/25g

352-11-4 Synthesis

352-11-4
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$5.00/25g

90754-65-7
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$60.00/100mg

Yield:90754-65-7 95%

Reaction Conditions:

with NHC-Pd(II)-Im;sodium hydroxide in water at 50; for 3 h;Inert atmosphere;Schlenk technique;

Steps:

Amination of benzyl chlorides 2 with dialkylformamides 3 in neat water catalysed by NHC-Pd(II)-Im complex 1; general procedure

General procedure: Under a N₂ atmosphere, NaOH (3.0 equiv), NHC-Pd(II)-Im complex 1 (1.0 mol%), water (1.0 mL), benzyl chloride 2a (0.8 mmol), and N-formylmorpholine 3a (2.0 equiv) were successively added into a Schlenk reaction tube. The mixture was stirred at 50 °C for 3 h. After cooling to room temperature, the reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous Na₂SO₄. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica gel (eluent: PE/EA = 5:1) to give the pure products 4a. 4-(4-Fluoro-benzyl)-morpholine (4k):¹⁶ Yellow liquid; 1H NMR (300 MHz): δ 7.30-7.25 (m, 2H), 7.02-6.96 (m, 2H), 3.69 (t, J = 4.5 Hz,4H), 3.44 (s, 2H), 2.41 (t, J = 4.5 Hz, 4H); 13C NMR (75 MHz): δ 161.6(d, J = 243.8 Hz), 133.4 (d, J = 3.2 Hz), 130.5 (d, J = 7.9 Hz), 114.9 (d,J = 21.0 Hz), 66.8, 62.5, 53.4.

References:

Chen, Wen-Xin;Zhang, Cai-Yun;Lu, Jian-Mei [Journal of Chemical Research,2013,vol. 37,# 10,p. 611 - 614]

4394-85-8 Synthesis

4394-85-8
309 suppliers
$6.00/25g