(R)-(+)-Bupivacaine Hydrochloride

Base Information

• Chemical Name: (R)-(+)-Bupivacaine Hydrochloride
• CAS No.: 27262-46-0
• Molecular Formula: C₁₈H₂₈N₂O*ClH
• Molecular Weight: 324.894
• DSSTox Substance ID: DTXSID90949994
• Wikidata: Q27146970
• ChEMBL ID: CHEMBL2447962
• Mol file: 27262-46-0.mol

Synonyms:(R)-(+)-Bupivacaine Hydrochloride;27262-46-0;(+)-Bupicaine HCl;Bupicaine hydrochloride (+);(+)-Bupicaine hydrochloride;(R)-bupivacaine hydrochloride;dextrobupivacaine hydrochloride;CHEBI:77442;(R)-(+)-Bupivacaine monohydrochloride;2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride, (+)-;(2R)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrochloride;( )-bupicaine Hydrochloride;2',6'-Pipecoloxylidide, 1-butyl-, monohydrochloride, ()-;CHEMBL2447962;dextrobupivacaine monohydrochloride;DTXSID90949994;2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, (R)-;(2R)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride;dextrobupivacaine hydrochloride (anhydrous);LS-109845;J-016714;Q27146970;(2R)-1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium chloride;1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid--hydrogen chloride (1/1)

Chemical Property of (R)-(+)-Bupivacaine Hydrochloride

Chemical Property:

• Vapor Pressure: 2.24E-07mmHg at 25°C
• Melting Point: 258 °C
• Boiling Point: 423.4°Cat760mmHg
• Flash Point: 209.9°C
• PSA: 32.34000
• Density: g/cm³
• LogP: 4.70940
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 324.1968412
• Heavy Atom Count: 22
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-BupivacaineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
• Isomeric SMILES: CCCCN1CCCC[C@@H]1C(=O)NC2=C(C=CC=C2C)C.Cl
• Uses: (R)-(+)-Bupivacaine monohydrochloride is a local anaesthetic used for epidural and intrathecal anaesthesia.

Technology Process of (R)-(+)-Bupivacaine Hydrochloride

There total 6 articles about (R)-(+)-Bupivacaine Hydrochloride 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: 96.0%

1-bromo-butane (109-65-9) + 2',6'-pipecoloxylidide (15883-20-2,27262-40-4,27262-43-7,78341-12-5) → bupivacaine hydrochloride (14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2)

Guidance literature:

1-bromo-butane; 2',6'-pipecoloxylidide; With tetrabutylammomium bromide; potassium carbonate; In toluene; at 80 - 85 ℃; for 5h; Green chemistry;

With hydrogenchloride; In water; toluene; Reagent/catalyst; Green chemistry;

Reference yield: 92.0%

→ bupivacaine hydrochloride (14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 80 - 85 ℃; for 8.5h;

With hydrogenchloride; In isopropyl alcohol; acetone; toluene; at 40 ℃;

Reference yield:

pipecolic Acid (4043-87-2,83680-83-5) → bupivacaine hydrochloride (14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / water / 12 h / 20 °C

2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C

2.2: 18 h / 20 °C

3.1: palladium on activated charcoal; hydrogen / methanol / 0.5 h / 50 °C / Autoclave

4.1: N,N-dimethyl-formamide / 12 h / 20 - 80 °C

4.2: 20 °C

With palladium on activated charcoal; hydrogen; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;

upstream raw materials:

pipecolic Acid

N-benzyloxycarbonyl D/L-pipecolinic acid

1-bromo-butane

2',6'-pipecoloxylidide

Downstream raw materials:

(+)-Bupivacaine

levobupivacaine

C₁₈H₂₈N₂O*C₄₂H₇₀O₃₅*ClH

racemic bupivacaine

Refernces

• 1、 -. "Preparation method of bupivacaine hydrochloride". . . Retrieved 2018/01/12.
• 2、 -. "Preparation process of bupivacaine hydrochloride". Paragraph 0024; 0025; 0026; 0027. . Retrieved 2017/07/20.