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ChemicalBook CAS DataBase List AKOS BBS-00007965
83708-39-8

AKOS BBS-00007965 synthesis

3synthesis methods
-

Yield:83708-39-8 45%

Reaction Conditions:

Stage #1: β-phenoxypropionitrilewith hydrogen in methanol at 110; under 30003 Torr; for 7 h;
Stage #2: with hydrogenchloride in ethyl acetate;Cooling with ice;

Steps:

3-phenoxypropan-1-amine hydrogen chloride (SZV-2017)

To a solution of 3-phenoxypropanenitrile (4.50 g, 30.00 mmol) in methanol (100 mL) Raney-Ni (1.20 g) was addedand the mixture was stirred at 110°C for 7 h under hydrogen (40 bar). After filtration the solvent was distilled off andthe crude product was purified with column chromatography (CHCl3:MeOH:H2O 60:12:1). The obtained product (2.80g) was dissolved in EtOAc-EtOH and EtOAc/HCl was added dropwise till pH 2-3. The precipitated crystals werefiltered off, washed with EtAOc and EtOH and dried under vacuum. White crystals (2.53 g, 45%), mp 175.0-176.0°C.1H NMR (DMSO-d6) δ (ppm): 8.10 (br s, 3H), 7.33-7.25 (m, 2H), 6.97-6.90 (m, 2H), 4.05 (t, J = 6.2 Hz, 2H), 2.94 (t, J = 7.3Hz, 2H), 2.02 (quint, J = 7.1 Hz, 2H). Anal. (C9H14ClNO) calcd. C 57.60; H 7.52; N 7.46. Found: C 57.47; H 7.26; N 7.38.

References:

Carpéné, Christian;Viana, Pénélope;Iffiú-Soltesz, Zsuzsa;Tapolcsányi, Pál;F?ldi, Anna ágota;Mátyus, Péter;Dunkel, Petra [Molecules,2022,vol. 27,# 19,art. no. 6224] Location in patent:supporting information

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