ChemicalBook CAS DataBase List (S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine synthesis

6synthesis methods

Product Name:(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine
CAS Number:132335-46-7
Molecular formula:C19H21NOS
Molecular Weight:311.44

321-38-0 Synthesis

321-38-0
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132335-44-5 Synthesis

(S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine

132335-44-5
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(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

132335-46-7
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Yield:132335-46-7 93.9%

Reaction Conditions:

Stage #1:(S)-3-dimethylamino-1-(2-thienyl)propan-1-ol with sodium hydride in dimethyl sulfoxide at 60; for 1.16667 h;
Stage #2:1-Fluoronaphthalene in dimethyl sulfoxide at 60; for 24 h;Solvent;Reagent/catalyst;

Steps:

2 Reference example 2 Preparation of dimethyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine
In a 500 mL four-necked flask, 18.5 g of (1S)-3-(dimethylamino)-1-(thiophen-2-yl)propan-1-ol was added.(0.1 mol) and 100 mL of DMSO. After stirring and dissolution, 8 g of sodium hydride (60% content) was added. After stirring for 10 minutes, it was heated to 60.°C, stirring for 1 hour; adding 17.5 g of 1-fluoronaphthalene (0.12 mol) at 60 °C, and keeping this temperature for 24 hours, reaction knotAfter the bundle is added 200mL of water and extracted twice with 100mL x 2 toluene, the toluene layer is combined and washed with 200mL x 2 water twicedimethyl[(3S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl]amine in toluene (purity 95.4%, isomer content4.7%, external standard content 29.2 g, yield 93.9%).

References:

Zhejiang Huahai Pharmaceutical Co., Ltd.;Zhejiang Huahai Licheng Pharmaceutical Co., Ltd.;Zhejiang Huahai Jiancheng Pharmaceutical Co., Ltd.;Liang Zunjun;Huang Jiansheng;Zhang Zheng;Tu Guoliang;Huang Wenfeng CN107382958, 2017, A Location in patent:Paragraph 0044-0052

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