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

Base Information

• Chemical Name: (R)-1,4-Benzodioxan-2-carboxypiperazine
• CAS No.: 860173-98-4
• Molecular Formula: C₁₃H₁₆N₂O₃
• Molecular Weight: 248.282
• DSSTox Substance ID: DTXSID80351047
• Wikidata: Q82127147
• Mol file: 860173-98-4.mol

Synonyms:860173-98-4;(R)-1,4-Benzodioxan-2-carboxypiperazine;(r)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone;[(3R)-2,3-dihydro-1,4-benzodioxin-3-yl]-piperazin-1-ylmethanone;(r)-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-piperazin-1-yl-methanone;DTXSID80351047;MFCD06796578;AS-37386;CS-0171461;A13362;(R)-1,4-benzodioxan-2-carboxypiperazine, AldrichCPR;1-[(2r)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperazine;(r)-(2,3-dihydrobenzo[1,4]dioxin-2-yl)-piperazin-1-yl-methanone

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

Chemical Property:

• Vapor Pressure: 7.62E-08mmHg at 25°C
• Refractive Index: 1.565
• Boiling Point: 437.2°C at 760 mmHg
• Flash Point: 218.2°C
• PSA: 50.80000
• Density: 1.246g/cm³
• LogP: 0.52490
• 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:

97% ^*data from raw suppliers

(R)-(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C(=O)C2COC3=CC=CC=C3O2
• Isomeric SMILES: C1CN(CCN1)C(=O)[C@H]2COC3=CC=CC=C3O2

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

There total 14 articles about (R)-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%

(R)-tert-butyl 4-(2,3-dihydrobenzo[b][1,4]dioxine-2-carbonyl)piperazine-1-carboxylate (1219800-50-6) → (R)-N-(1,4-benzodioxan-2-carbonyl)piperazine (860173-98-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1.41667h;

Reference yield:

methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate (3663-79-4,650597-66-3) → (R)-N-(1,4-benzodioxan-2-carbonyl)piperazine (860173-98-4)

Guidance literature:

Multi-step reaction with 3 steps

1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1

2: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 0 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; di-isopropyl ether;

DOI:10.1016/j.tetasy.2012.10.018

Reference yield:

1,4-benzodioxin-2-carboxylic acid (67471-01-6) → (R)-N-(1,4-benzodioxan-2-carbonyl)piperazine (860173-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux

2: triethylamine / dichloromethane / 2 h / 0 - 25 °C

3: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; (S,R)-ZhaoPhos / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave

4: trifluoroacetic acid / dichloromethane / 6 h / 0 - 20 °C

With bis(norbornadiene)rhodium(l)tetrafluoroborate; thionyl chloride; (S,R)-ZhaoPhos; hydrogen; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/acs.orglett.8b01469

upstream raw materials:

(R)-methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate

methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate

(+)-(2R)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid

(R)-tert-butyl 4-(2,3-dihydrobenzo[b][1,4]dioxine-2-carbonyl)piperazine-1-carboxylate

Downstream raw materials:

(R)-doxazosin