(S)-1,4-Benzodioxan-2-carboxypiperazine

Base Information

• Chemical Name: (S)-1,4-Benzodioxan-2-carboxypiperazine
• CAS No.: 401941-54-6
• Molecular Formula: C₁₃H₁₆N₂O₃
• Molecular Weight: 248.282
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20351046
• Nikkaji Number: J1.700.762I
• Wikidata: Q82127144
• Mol file: 401941-54-6.mol

Synonyms:(S)-1,4-Benzodioxan-2-carboxypiperazine;401941-54-6;(S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone;[(3S)-2,3-dihydro-1,4-benzodioxin-3-yl]-piperazin-1-ylmethanone;DTXSID20351046;BRA94154;(S)-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)-piperazin-1-yl-methanone;MFCD03426389;Piperazine, 1-[[(2S)-2,3-dihydro-1,4-benzodioxin-2-yl]carbonyl]-;AKOS015963245;AS-37384;CS-0171460;(s)-1-(1,4-benzodioxan-2-carboxy)piperazine

Chemical Property of (S)-1,4-Benzodioxan-2-carboxypiperazine

Chemical Property:

• Vapor Pressure: 7.62E-08mmHg at 25°C
• Refractive Index: 1.565
• Boiling Point: 437.2°Cat760mmHg
• Flash Point: 218.2°C
• PSA: 50.80000
• Density: 1.246g/cm³
• LogP: 0.52490
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 248.11609238
• Heavy Atom Count: 18
• Complexity: 305

Purity/Quality:

98%min ^*data from raw suppliers

(S)-1,4-Benzodioxan-2-carboxypiperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN(CCN1)C(=O)C2COC3=CC=CC=C3O2
• Isomeric SMILES: C1CN(CCN1)C(=O)[C@@H]2COC3=CC=CC=C3O2
• Uses: (S)-1,4-Benzodioxan-2-carboxypiperazine is the key chiral intermediate for the synthesis of (S)-doxazosin (D537500, Mesylate salt), a selective α1-adrenoceptor antagonist. Doxazosin relaxes smooth muscles of the prostate.

Technology Process of (S)-1,4-Benzodioxan-2-carboxypiperazine

There total 9 articles about (S)-1,4-Benzodioxan-2-carboxypiperazine 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%

(S)-N-Boc-(1,4-benzodioxan-2-carbonyl)piperazine (1415584-44-9) → (S)-N-(1,4-benzodioxan-2-carbonyl)piperazine (401941-54-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.tetasy.2012.10.018

Reference yield:

piperazine (110-85-0) + (S)-2,3-dihydrobenzo[1,4]dioxine-2-carbonyl chloride (401947-96-4) → (S)-N-(1,4-benzodioxan-2-carbonyl)piperazine (401941-54-6)

Guidance literature:

With hydrogenchloride; In methanol; water; at 30 - 35 ℃; for 4.5h;

DOI:10.1016/S0957-4166(01)00368-8

Reference yield:

(S)‐1,4‐benzodioxane‐2‐carboxylic acid (70918-54-6) → (S)-N-(1,4-benzodioxan-2-carbonyl)piperazine (401941-54-6)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / CDCl₃ / 1.5 h / 84 °C

2: 1.86 kg / conc. HCl / H₂O; methanol / 4.5 h / 30 - 35 °C

With hydrogenchloride; thionyl chloride; In methanol; chloroform-d1; water;

DOI:10.1016/S0957-4166(01)00368-8

upstream raw materials:

piperazine

(S)-2,3-dihydrobenzo[1,4]dioxine-2-carbonyl chloride

ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate

benzene-1,2-diol

Downstream raw materials:

(S)-doxazosin

(+)-(S)-doxazosin mesylate

Refernces

• 1、 Rouf, Abdul,Gupta, Pankaj,Aga, Mushtaq A.,Kumar, Brijesh,Chaubey, Asha,Parshad, Rajinder,Taneja, Subhash C.. "Chemoenzymatic synthesis of piperoxan, prosympal, dibozane, and doxazosin". . p. 1615 - 1623. Retrieved 2013/02/22.