cis-4-(3-(Diethylamino)propynyl)-1,3-dimethyl-6-(4-fluorophenyl)-3,4-piperidinediol

Base Information

• Chemical Name: cis-4-(3-(Diethylamino)propynyl)-1,3-dimethyl-6-(4-fluorophenyl)-3,4-piperidinediol
• CAS No.: 120768-88-9
• Molecular Formula: C₂₀H₂₉FN₂O₂
• Molecular Weight: 348.461
• DSSTox Substance ID: DTXSID80153003
• Wikidata: Q76279522
• Mol file: 120768-88-9.mol

Synonyms:BRN 3565328;3,4-Piperidinediol, 4-(3-(diethylamino)-1-propynyl)-1,3-dimethyl-6-(4-fluorophenyl)-, (3-alpha,4-beta,6-beta)-;cis-4-(3-(Diethylamino)propynyl)-1,3-dimethyl-6-(4-fluorophenyl)-3,4-piperidinediol;120768-88-9;3,4-Piperidinediol, 4-(3-(diethylamino)-1-propynyl)-6-(4-fluorophenyl)-1,3-dimethyl-, (3alpha,4beta,6beta)-;C20H29FN2O2;DTXSID80153003;C20-H29-F-N2-O2;LS-115153

Chemical Property of cis-4-(3-(Diethylamino)propynyl)-1,3-dimethyl-6-(4-fluorophenyl)-3,4-piperidinediol

Chemical Property:

• Vapor Pressure: 4.1E-09mmHg at 25°C
• Boiling Point: 456.2°Cat760mmHg
• Flash Point: 229.7°C
• Density: 1.17g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 348.22130633
• Heavy Atom Count: 25
• Complexity: 504

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CC#CC1(CC(N(CC1(C)O)C)C2=CC=C(C=C2)F)O
• Isomeric SMILES: CCN(CC)CC#C[C@@]1(C[C@H](N(C[C@]1(C)O)C)C2=CC=C(C=C2)F)O

Technology Process of cis-4-(3-(Diethylamino)propynyl)-1,3-dimethyl-6-(4-fluorophenyl)-3,4-piperidinediol

There total 3 articles about cis-4-(3-(Diethylamino)propynyl)-1,3-dimethyl-6-(4-fluorophenyl)-3,4-piperidinediol 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: 71.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (3S,4R,6S)-4-Ethynyl-6-(4-fluoro-phenyl)-1,3-dimethyl-piperidine-3,4-diol (120729-81-9,121368-78-3) + diethylamine (109-89-7) → (3S,4R,6S)-4-(3-Diethylamino-prop-1-ynyl)-6-(4-fluoro-phenyl)-1,3-dimethyl-piperidine-3,4-diol (120768-88-9)

Guidance literature:

With copper(I) chloride; In 1,4-dioxane; for 6h; Heating;

DOI:10.1007/BF00764463

Reference yield:

(E)-3-(4-Fluoro-phenyl)-1-(2-methyl-oxiranyl)-propenone (31374-65-9) → (3S,4R,6S)-4-(3-Diethylamino-prop-1-ynyl)-6-(4-fluoro-phenyl)-1,3-dimethyl-piperidine-3,4-diol (120768-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1: benzene / 1 h / 150 °C

2: 84 percent / liquid ammonia; diethyl ether / 1 h

3: 71 percent / Cu₂Cl₂ / dioxane / 6 h / Heating

With copper(I) chloride; In 1,4-dioxane; diethyl ether; ammonia; benzene;

DOI:10.1007/BF00764463

Reference yield:

3e-hydroxy-1e,3a-dimethyl-6e-(4-fluorophenyl)-4-piperidone (36106-54-4,60054-02-6,103021-98-3) → (3S,4R,6S)-4-(3-Diethylamino-prop-1-ynyl)-6-(4-fluoro-phenyl)-1,3-dimethyl-piperidine-3,4-diol (120768-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / liquid ammonia; diethyl ether / 1 h

2: 71 percent / Cu₂Cl₂ / dioxane / 6 h / Heating

With copper(I) chloride; In 1,4-dioxane; diethyl ether; ammonia;

DOI:10.1007/BF00764463

upstream raw materials:

formaldehyd

(3S,4R,6S)-4-Ethynyl-6-(4-fluoro-phenyl)-1,3-dimethyl-piperidine-3,4-diol

diethylamine

(E)-3-(4-Fluoro-phenyl)-1-(2-methyl-oxiranyl)-propenone