tert-Butyl 4-(2-bromophenyl)piperazine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 4-(2-bromophenyl)piperazine-1-carboxylate
• CAS No.: 494773-35-2
• Molecular Formula: C15H21BrN2O2
• Molecular Weight: 341.248
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID20585965
• Wikidata: Q72511151
• Mol file: 494773-35-2.mol

Synonyms:494773-35-2;tert-Butyl 4-(2-bromophenyl)piperazine-1-carboxylate;1-BOC-4-(2-Bromophenyl)piperazine;4-(2-BROMO-PHENYL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;4-(2-Bromophenyl)piperazine-1-carboxylic acid tert-butyl ester;SCHEMBL1928396;DTXSID20585965;QEKMJBDSLYRIKY-UHFFFAOYSA-N;AMY32322;MFCD08064040;N1-BOC-4-(2-Bromophenyl)piperazine;AKOS015897826;AB43504;PS-7008;AC-29061;4-(2-Bromophenyl)piperazine, N1-BOC protected;EN300-7361192;A871800;4-(2-Bromophenyl)-piperazine-1-carboxylic acid, t-butyl ester;4-(2-Bromophenyl)piperazine-1-carboxylic acid tert butyl ester

Chemical Property of tert-Butyl 4-(2-bromophenyl)piperazine-1-carboxylate

Chemical Property:

• Boiling Point: 412.8±40.0 °C(Predicted)
• PKA: 1.88±0.10(Predicted)
• PSA: 32.78000
• Density: 1.332
• LogP: 3.50910
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 340.07864
• Heavy Atom Count: 20
• Complexity: 335

Purity/Quality:

98%min ^*data from raw suppliers

4-(2-Bromophenyl)piperazine-1-carboxylicAcidTert-butylEster ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2Br
• Uses: 4-(2-Bromophenyl)piperazine-1-carboxylic Acid Tert-butyl Ester is used in the synthesis of Vortioxetine Hydrobromide which is a drug used in the treatment of depression.

Technology Process of tert-Butyl 4-(2-bromophenyl)piperazine-1-carboxylate

There total 7 articles about tert-Butyl 4-(2-bromophenyl)piperazine-1-carboxylate 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: 74.9%

1-[1,1-dimethylethoxycarbonyl]-4-(2-aminophenyl)piperazine (170017-74-0) → 4-(2-bromophenyl)piperazine-1-carboxylic acid tert-butyl ester (494773-35-2)

Guidance literature:

1-[1,1-dimethylethoxycarbonyl]-4-(2-aminophenyl)piperazine; With sulfuric acid; sodium nitrite; In water; at 0 - 20 ℃;

With sodium bromide; copper(I) bromide; In water; at 80 ℃; for 3h; Reagent/catalyst;

Reference yield: 68.0%

1-t-Butoxycarbonylpiperazine (57260-71-6) + 2,3-dibromobenzene (583-53-9) → 4-(2-bromophenyl)piperazine-1-carboxylic acid tert-butyl ester (494773-35-2)

Guidance literature:

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 80 ℃; for 24h;

DOI:10.1016/j.tet.2008.01.070

Reference yield:

1-Bromo-2-iodobenzene (583-55-1) + piperazine-1-carboxylic acid phenyl ester (50606-33-2) + tert-butyl alcohol (75-65-0) → 4-(2-bromophenyl)piperazine-1-carboxylic acid tert-butyl ester (494773-35-2) + 1-(2-bromophenyl)piperazine (1011-13-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate; In toluene; at 110 ℃; for 10h; Temperature; Overall yield = 128.1 g; Inert atmosphere;

upstream raw materials:

1-t-Butoxycarbonylpiperazine

2,3-dibromobenzene

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

1-[1,1-dimethylethoxycarbonyl]-4-(2-aminophenyl)piperazine

Downstream raw materials:

1-[2-(4-methoxyphenyl)phenyl]piperazine

1-[2-(4-hydroxyphenyl)phenyl]piperazine

4-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine-1-carboxylic acid tert-butyl ester

tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate

Refernces

• 1、 -. "PYRIDAZINONES AND METHODS OF USE THEREOF". Page/Page column 230; 231. . Retrieved 2019/04/11.
• 2、 -. "NEW VORTIOXETINE INTERMEDIATE AND SYNTHESIS PROCESS THEREOF". . . Retrieved 2017/04/12.