Reserpiline

Base Information

• Chemical Name: Reserpiline
• CAS No.: 131-02-2
• Deprecated CAS: 1356-83-8,37338-41-3,493020-80-7
• Molecular Formula: C23H28 N2 O5
• Molecular Weight: 412.486
• European Community (EC) Number: 205-005-3
• UNII: C0N6EP99UK
• DSSTox Substance ID: DTXSID20927028
• Nikkaji Number: J10.012I
• Wikidata: Q27275019
• Mol file: 131-02-2.mol

Synonyms:Reserpiline;Elliptamine;Reserpilin;131-02-2;(-)-Reserpiline;EINECS 205-005-3;UNII-C0N6EP99UK;C0N6EP99UK;Methyl (3beta,19alpha,20alpha)-16,17-didehydro-10,11-dimethoxy-19-methyloxayohimban-16-carboxylate;Methyl 16,17-didehydro-10,11-dimethoxy-19alpha-methyl-18-oxa-3beta,20alpha-yohimban-16-carboxylat;Reserpiline hydrochloride;methyl (4S,4aS,13bR,14aS)-10,11-dimethoxy-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate;Oxayohimban-16-carboxylic acid, 16,17-didehydro-10,11-dimethoxy-19-methyl-, methyl ester, (3-beta,19-alpha,20-alpha)-;RESERPILINE [MI];RESERPILINE [WHO-DD];SCHEMBL355882;DTXSID20927028;CHEBI:135667;Oxayohimban-16-carboxylic acid, 16,17-didehydro-10,11-dimethoxy-19-methyl-, methyl ester, (3.beta.,19.alpha.,20.alpha.)-;AKOS040753731;LS-99744;Q27275019;methyl 10,11-dimethoxy-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate;(3-beta,19-alpha,20-alpha)-16,17-Didehydro-10,11-dimethoxy-19-methyloxayohimban-16-carboxylic acid methyl ester;4H-INDOLO(2,3-A)PYRANO(3,4-G)QUINOLIZINE-1-CARBOXYLIC ACID, 4A,5,7,8,13,13B,14,14A-OCTAHYDRO-10,11-DIMETHOXY-4-METHYL-, METHYL ESTER, (4S,4AS,13BR,14AS)-;methyl (1R,15S,16S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

Chemical Property of Reserpiline

Chemical Property:

• Vapor Pressure: 5.34E-13mmHg at 25°C
• Boiling Point: 569.9°Cat760mmHg
• PKA: 17.95±0.60(Predicted)
• Flash Point: 298.4°C
• PSA: 73.02000
• Density: 1.31g/cm³
• LogP: 3.13390
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 412.19982200
• Heavy Atom Count: 30
• Complexity: 699

Purity/Quality:

98%min ^*data from raw suppliers

Methyl(3beta,19alpha,20alpha)-16,17-didehydro-10,11-dimethoxy-19-methyloxayohimban-16-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC(=C(C=C45)OC)OC
• Isomeric SMILES: C[C@H]1[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC(=C(C=C45)OC)OC
• Description: An amorphous alkaloid present in Rauwolfia canescens and R. serpentina, the alkaloid forms several crystalline salts and derivatives including the hydrochloride, m.p. 205-7°C; [α]24D - 40° (c 0.44, EtOH); the tartrate, m.p. 190- 2°C; [α]20D - 50° (c 1.0, H20); the oxalate, m.p. 252°C; [α]20D - 4° (c 0.2, aqueous EtOH); the picrate, m.p. 173°C and the di-p-toluyl-L-tartrate, m.p. 194- 5° C (dec.).

Technology Process of Reserpiline

There total 8 articles about Reserpiline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 2.5%

(1S,4aS,8aS)-7-[2-(5,6-Dimethoxy-1H-indol-3-yl)-ethyl]-1-methyl-7-oxy-4a,5,6,7,8,8a-hexahydro-1H-pyrano[3,4-c]pyridine-4-carboxylic acid methyl ester (81633-50-3,81655-39-2) → (1S,4aS,13cS)-10,11-Dimethoxy-1-methyl-4a,5,6,7,8,13,13b,13c-octahydro-1H-2-oxa-6a,13-diaza-indeno[1,2-c]phenanthrene-4-carboxylic acid methyl ester (81633-51-4) + isoreserpiline (572-67-8) + reserpiline (131-02-2)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; at -78 - 5 ℃; for 2h;

Reference yield:

2,3-seco-2,3-dihydroreserpiline (68753-63-9) → (1S,4aS,13cS)-10,11-Dimethoxy-1-methyl-4a,5,6,7,8,13,13b,13c-octahydro-1H-2-oxa-6a,13-diaza-indeno[1,2-c]phenanthrene-4-carboxylic acid methyl ester (81633-51-4) + isoreserpiline (572-67-8) + reserpiline (131-02-2)

Guidance literature:

With sodium tetrahydroborate; mercury(II) diacetate; Yield given. Multistep reaction. Yields of byproduct given; 1.) acetic acid, H₂O, 90 deg C, 1.5 h;

Reference yield:

2-Chloro-1-(5,6-dimethoxy-1H-indol-3-yl)ethanone (81633-43-4) → reserpiline (131-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / NaHCO₃ / dimethylformamide / 3 h / 60 °C

2: 72 percent / NaBH₄, acetic acid / dioxane / 2 h / Heating

3: 1.) Hg(AcO)2, 2.) NaBH₄ / 1.) acetic acid, H₂O, 90 deg C, 1.5 h

With sodium tetrahydroborate; mercury(II) diacetate; sodium hydrogencarbonate; acetic acid; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

2,3-seco-2,3-dihydroreserpiline

(1S,4aS,8aS)-7-[2-(5,6-Dimethoxy-1H-indol-3-yl)-ethyl]-1-methyl-7-oxy-4a,5,6,7,8,8a-hexahydro-1H-pyrano[3,4-c]pyridine-4-carboxylic acid methyl ester

2-Chloro-1-(5,6-dimethoxy-1H-indol-3-yl)ethanone

5,6-dimethoxyindole

Downstream raw materials:

carapanaubine

iso-carapanaubine

ent-7-acetoxy-10,11-dimethoxy-19β-methyl-(7ξ,15β)-7H-18-oxa-yohimb-16-ene-16-carboxylic acid methyl ester