hydron;2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;chloride

Base Information

• Chemical Name: hydron;2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;chloride
• CAS No.: 134-63-4
• Molecular Formula: C22H28ClNO2
• Molecular Weight: 373.923
• Mol file: 134-63-4.mol

Synonyms:

Chemical Property of hydron;2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;chloride

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 3.02E-11mmHg at 25°C
• Melting Point: 183-185 °C (dec.)(lit.)
• Refractive Index: -57.5 ° (C=1, H2O)
• Boiling Point: 485.6 °C at 760 mmHg
• Flash Point: 247.5 °C
• PSA: 40.54000
• LogP: 4.97590
• Storage Temp.: Store at RT
• Solubility.: H2O: 25 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 373.1808568
• Heavy Atom Count: 26
• Complexity: 412

Purity/Quality:

99% ^*data from raw suppliers

a-Lobeline Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [H+].CN1C(CCCC1CC(=O)C2=CC=CC=C2)CC(C3=CC=CC=C3)O.[Cl-]
• Isomeric SMILES: [H+].CN1[C@@H](CCC[C@@H]1CC(=O)C2=CC=CC=C2)C[C@@H](C3=CC=CC=C3)O.[Cl-]
• Description: (–)-Lobeline is an alkaloid that has been found in Lobelia and has diverse biological activities. It binds to nicotinic acetylcholine receptors (nAChRs) in rat brain homogenates (Ki = 4 nM) and has antinociceptive effects in the tail-flick assay in mice. (–)-Lobeline (0.3 and 0.9 mg/kg) reduces the number of errors in a repeated acquisition procedure in the radial arm maze in rats. It also decreases immobility time in the forced swim test and feeding latency in the novelty suppressed feeding test, indicating antidepressant-like activity, in mice when administered at doses of 1 and 4 mg/kg.
• Uses: A neuronal nicotinic acetylcholine receptor agonist. A respiratory stimulant A neuronal nicotinic acetylcholine receptor agonist. A CNS stimulant.

Technology Process of hydron;2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;chloride

There total 8 articles about hydron;2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;chloride 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:

(S)-2-[(2R,6S)-6-(2-propionyloxy-2-phenylethyl)-1-methylpiperidin-2-yl]-1-phenylethanone (950194-40-8) → Lobeline hydrochloride (134-63-4)

Guidance literature:

With hydrogenchloride; In methanol; Heating;

DOI:10.1021/ol071064i

Reference yield:

C25H33NO3 (950194-38-4) → Lobeline hydrochloride (134-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: CrO₃; H₂SO₄ / acetone / 1 h / 20 °C

2: aq. HCl / methanol / Heating

With chromium(VI) oxide; hydrogenchloride; sulfuric acid; In methanol; acetone;

DOI:10.1021/ol071064i

Reference yield:

2,2′-((2,6)-1-methylpiperidine-2,6-diyl)bis(1-phenylethanone) hydrochloride (6168-88-3) → Lobeline hydrochloride (134-63-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / NaBH₄ / methanol / 20 °C

2: 92 percent / (S)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; Na₂SO₄ / CDCl₃ / 48 h / 20 °C

3: CrO₃; H₂SO₄ / acetone / 1 h / 20 °C

4: aq. HCl / methanol / Heating

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; sulfuric acid; sodium sulfate; In methanol; chloroform-d1; acetone;

DOI:10.1021/ol071064i

upstream raw materials:

(S)-2-[(2R,6S)-6-(2-propionyloxy-2-phenylethyl)-1-methylpiperidin-2-yl]-1-phenylethanone

C₂₅H₃₃NO₃

2,2′-((2,6)-1-methylpiperidine-2,6-diyl)bis(1-phenylethanone) hydrochloride

NSC 95097

Downstream raw materials:

lobeline

(R)-2-((2R,6S)-1-Methyl-6-phenethyl-piperidin-2-yl)-1-phenyl-ethanol

cis-2S,6R-N-methyl-6-phenacyl-2-trans-styrylpiperidine

(S)-2-[(2S,6R)-1-Methyl-6-((E)-styryl)-piperidin-2-yl]-1-phenyl-ethanol

Refernces

• 1、 Krishnan, Shyam,Bagdanoff, Jeffrey T.,Ebner, David C.,Ramtohul, Yeeman K.,Tambar, Uttam K.,Stoltz, Brian M.. "Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: Applications to the total synthesis of alkaloids". supporting information; experimental part. p. 13745 - 13754. Retrieved 2009/02/06.