116817-13-1

Basic information

• Product Name: 2-Thiophenepropanamine,N-methyl-g-(1-naphthalenyloxy)-
• Synonyms: (?à)-Duloxetine; N-Methyl-3-(1-naphthoxy)-3-(2-thienyl)propylamine
• CAS NO: 116817-13-1
• Molecular Formula: C₁₈H₁₉NOS
• Molecular Weight: 297.4146
• Mol File: 116817-13-1.mol
• Article Data: 69

Chemical Properties

• Boiling Point: 466.2°Cat760mmHg
• Flash Point: 235.7°C
• Density: 1.158g/cm³
• PKA: 10.02±0.10(Predicted)
• CAS DataBase Reference: 2-Thiophenepropanamine,N-methyl-g-(1-naphthalenyloxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiophenepropanamine,N-methyl-g-(1-naphthalenyloxy)-(116817-13-1)
• EPA Substance Registry System: 2-Thiophenepropanamine,N-methyl-g-(1-naphthalenyloxy)-(116817-13-1)

Safety Data

• Hazardous Substances Data: 116817-13-1(Hazardous Substances Data)

Upstream product

• 178273-35-3 (S)-Norduloxetine 
• 74-88-4 methyl iodide 
• 136434-34-9 duloxetine hydrochloride 
• 13636-02-7 3-(N,N-dimethylamino)-1-(thien-2-yl)propan-1-ol 
• 74-89-5 methylamine 
• 14756-03-7 3-(2-thienyl)acrolein 
• 90-15-3 α-naphthol 
• 116539-58-3 Duloxetine 
• 1374030-94-0 (S)-3-(diallylamino)-1-(thiophen-2-yl)propan-1-ol 
• 98-03-3 thiophene-2-carbaldehyde 
• 802269-27-8 3-[methoxy(methyl)amino]-1-(2-thienyl)-1-propanone 
• 321-38-0 1-Fluoronaphthalene 
• 116817-86-8 (+)-(S)-N-methyl-γ-(1-naphthyloxy)-2-thiophenepropylamine maleate 
• 1242592-77-3 N-methyl-N-methoxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 

Downstream Products

• 949096-01-9 (+/-)-N-methyl-3-(2-thienyl)-3-(4-hydroxy-naphtyl)-propylamine hydrogenbromide 
• 116817-86-8 (+)-(S)-N-methyl-γ-(1-naphthyloxy)-2-thiophenepropylamine maleate 
• 136434-34-9 duloxetine hydrochloride 
• 1369583-87-8 N-[4-(2-methoxyphenylpiperazinyl)propionyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-88-9 N-[4-(3-trifluoromethylphenylpiperazinyl)propionyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-90-3 N-[4-(4-(2-methoxyphenylpiperazinyl)butyryl)]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-91-4 N-[4-(4-(3-trifluoromethylphenylpiperazinyl)butyryl)]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-93-6 N-[4-(2-methoxyphenylpiperazinyl)propyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 132335-46-7 N-methyl-(S)-duloxetine 
• 116539-60-7 (R)-Duloxetine 
• 116539-58-3 Duloxetine 

Relevant articles and documents

Preparation method of duloxetine

To the method, 1 - naphthol and 3 - (2 - thienyl) -2 - acrolein serve as starting materials, and (S)-3 - (1 - naphthyloxy) -3 - (2 - thienyl) propanal is obtained through addition reaction under the action of a catalyst. The raw materials are cheap and easily available, and 1 - fluoronaphthalene which is expensive is not needed. Sodium hydride and operation are tedious, the cost is low, the process operation is safe and convenient, the three wastes are small in generation amount, and green and environment-friendly. The reaction atom economy is high, the reaction selectivity of each step is high, the side reaction is small, the optical purity and yield of the target product are high, and the green industrial production is facilitated.

Anti-depression of the raw material preparation method

The present invention discloses an anti-depression drug duloxetine hydrochloride - process improvement and optimization, which belongs to the field of biological medicine. Comprises the following main features: a) used in the Mannich reaction in N - methyl benzylamine hydrochloride, without the use of dimethylamine hydrochloride, so that the follow-up steps in the dealkylation reaction effect is better, yield is higher; b) without using any expensive chiral catalyst or a phase transfer catalyst, to use with high stability and high catalytic performance of metal catalyst; c) the better solvent for crystallization and to the solvent method, to avoid the harm of the residual solvent for crystallization; d) splitting the chiral compound in the dealkylation after, adopts a unique recrystallization technology, will split the mixture after separation, purity and relatively easy to assemble and disassemble the luminosity (S)- N - methyl - 3 - (1 - naphthoxy) - 3 - (2 - thienyl) propylamine/tartrate, so that the resulting duloxetine hydrochloride product can achieve a better therapeutic effect. The process of the invention clear, simple and convenient operation, mild reaction conditions, low production cost, is extremely beneficial to industrial production.

Preparation method for chiral gamma-sec-amino-alcohol

The invention provides a preparation method for chiral gamma-sec-amino-alcohol. The preparation method is characterized in that an acid addition salt of beta-sec-amino-ketone as shown in a general formula (I) which is described in the specification, alkali, a metal salt additive and a bisphosphine-rhodium complex are added into a solvent and a reaction is carried out in a hydrogen atmosphere so as to produce a chiral gamma-sec-amino-alcohol compound as shown in a general formula (II) which is described in the specification; and in the general formula (I) and the general formula (II), Ar represents an aryl group with or without substituent, R represents an alkyl group or aralkyl group, and HY represents acid. The preparation method is simple in synthesis route and process; the metal salt additive substantially improves the technical effect of rhodium in catalysis of asymmetric hydrogenation and enhances reaction yield and optical purity of the product; and production process is simplified, production cost is lowered, and the preparation method is suitable for industrial large-scale production.