116817-84-6

Basic information

• Product Name: S-(+)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)-1-propylamide
• Synonyms: (S)-3-(DiMethylaMino)-1-(thiophen-3-yl)propan-1-ol;rac-α-[2-(Dimethylamino)ethyl]-3-thiophenemethanol;S-(+)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)-1-propylamide;3-THIOPHENEMETHANOL, A-[2-(DIMETHYLAMINO)ETHYL]-;S-(-)-N,N-DIMETHYL-3-HYDROXY-2-THIENYLPROPANAMINE;S(+)-N,N-DIMETHYL-3-HYDROXY-3-(2-THIENYL)-1-PROPANAMINE;(S)-1-b-Hydroxy-1-(2-thienyl)-3-dimethylaminopropane;3-THIOPHENEMETHANOL, A-[2-(DIMETHYLAMINO)ETHYL]-(9CI)
• CAS NO: 116817-84-6
• Molecular Formula: C₉H₁₅NOS
• Molecular Weight: 185.2865
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 116817-84-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 74-76°C
• Boiling Point: 290.1±30.0 °C(Predicted)
• Appearance: /
• Density: 1.111±0.06 g/cm3(Predicted)
• Storage Temp.: Room Temperature, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.35±0.20(Predicted)
• CAS DataBase Reference: S-(+)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)-1-propylamide(CAS DataBase Reference)
• NIST Chemistry Reference: S-(+)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)-1-propylamide(116817-84-6)
• EPA Substance Registry System: S-(+)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)-1-propylamide(116817-84-6)

Safety Data

• Hazardous Substances Data: 116817-84-6(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 116817-84-6 differently. You can refer to the following data:
1. S-(+)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)-1-propylamide is a useful synthetic intermediate.
2. rac-α-[2-(Dimethylamino)ethyl]-3-thiophenemethanol is an intermediate in the synthesis of rac Duloxetine 3-Thiophene Isomer (D721025). rac Duloxetine 3-Thiophene Isomer Hydrochloride is an isomeric impurity of the antidepressant Duloxetine Hydrochloride (D721000).

Synthetic route

3-(dimethylamino)-1-(thiophen-3-yl)propan-1-one (100860-96-6) → α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6)

Conditions	Yield
With sodium tetrahydroborate; potassium carbonate In methanol

1-(thiophen-3-yl)-ethanone (1468-83-3) → α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / ethanol 2: aq. K2CO3; NaBH4 / methanol View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water; isopropyl alcohol / 6 h / 82 - 83 °C 2: sodium hydroxide; sodium tetrahydroborate / ethanol / 4 h / 20 - 30 °C / Cooling with ice View Scheme

3-(dimethylamino)-1-(thiophen-3-yl)propan-1-one hydrochloride (14994-02-6) → α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6)

Conditions	Yield
	29.0 g (47.7%)
With sodium tetrahydroborate; sodium hydroxide In ethanol at 20 - 30℃; for 4h; Cooling with ice;

1-Fluoronaphthalene (321-38-0) + α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6) → N,N-dimethyl-3-(1-naphthalenyloxy)-3-(3-thienyl)propanamine (116817-25-5)

Conditions	Yield
With 2,4-dichlorophenoxyacetic acid dimethylamine; sodium hydride

α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6) → methyl-[3-(naphthalen-1-yloxy)-3-thiophen-3-yl-propyl]-amine

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH; DMA 2: toluene 3: NaOH; propylene glycol View Scheme

α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6) → methyl-[3-(naphthalen-1-yloxy)-3-thiophen-3-yl-propyl]-carbamic acid phenyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH; DMA 2: toluene View Scheme

α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6) → 9-hydroxy-2-methyl-3-(2-(methyl((S)-3-(naphthalen-1-yloxy)-3-(thiophen-3-yl)propyl)amino)ethyl)-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogenchloride / water; tert-butyl methyl ether / 0.17 h / pH 1 - 1.5 1.2: 1 h / Reflux 2.1: sodium hydroxide / water; ethyl acetate / pH 11 3.1: sodium hydride / water; dimethyl sulfoxide / 0.5 h 3.2: 0.5 h 4.1: ammonia / water; toluene / 1 h 4.2: 1 h / 55 °C 5.1: potassium carbonate; 18-crown-6 ether / tetrahydrofuran / Reflux View Scheme

α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6) → C9H15NOS

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water; tert-butyl methyl ether / 0.17 h / pH 1 - 1.5 1.2: 1 h / Reflux 2.1: sodium hydroxide / water; ethyl acetate / pH 11 View Scheme

α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6) → C19H21NOS*C2H2O4

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water; tert-butyl methyl ether / 0.17 h / pH 1 - 1.5 1.2: 1 h / Reflux 2.1: sodium hydroxide / water; ethyl acetate / pH 11 3.1: sodium hydride / water; dimethyl sulfoxide / 0.5 h 3.2: 0.5 h View Scheme

α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6) → C18H19NOS*C2H2O4

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water; tert-butyl methyl ether / 0.17 h / pH 1 - 1.5 1.2: 1 h / Reflux 2.1: sodium hydroxide / water; ethyl acetate / pH 11 3.1: sodium hydride / water; dimethyl sulfoxide / 0.5 h 3.2: 0.5 h 4.1: ammonia / water; toluene / 1 h 4.2: 1 h / 55 °C View Scheme

(S)-Mandelic acid (17199-29-0) + α-[2-(Dimethylamino)ethyl]-3-thiophene methanol (116817-84-6) → C9H15NOS*C8H8O3

Conditions	Yield
Stage #1: α-[2-(Dimethylamino)ethyl]-3-thiophene methanol With hydrogenchloride In tert-butyl methyl ether; water for 0.166667h; pH=1 - 1.5; Stage #2: (S)-Mandelic acid In ethanol for 1h; Reflux;	21.41 g

Upstream product

• 100860-96-6 3-(dimethylamino)-1-(thiophen-3-yl)propan-1-one 
• 1468-83-3 1-(thiophen-3-yl)-ethanone 
• 14994-02-6 3-(dimethylamino)-1-(thiophen-3-yl)propan-1-one hydrochloride 

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