Benzyl spiro[indoline-3,4'-piperidine]-1'-carboxylate

Base Information

• Chemical Name: Benzyl spiro[indoline-3,4'-piperidine]-1'-carboxylate
• CAS No.: 167484-18-6
• Molecular Formula: C20H22N2O2
• Molecular Weight: 322.407
• Hs Code.: 2933990090
• European Community (EC) Number: 848-470-3
• DSSTox Substance ID: DTXSID201151979
• Nikkaji Number: J891.226B
• Mol file: 167484-18-6.mol

Synonyms:167484-18-6;Benzyl spiro[indoline-3,4'-piperidine]-1'-carboxylate;1'-(BENZYLOXYCARBONYL)SPIRO(INDOLINE-3,4'-PIPERIDINE);1'-CBZ-SPIRO[INDOLINE-3,4'-PIPERIDINE];benzyl 1,2-dihydrospiro[indole-3,4'-piperidine]-1'-carboxylate;Benzyl Spiro[1,2-dihydroindole-3,4'-piperidine]-1'-carboxylate;1/'-(BENZYLOXYCARBONYL)SPIRO(INDOLINE-3,4/'-PIPERIDINE);SPIRO[3H-INDOLE-3,4'-PIPERIDINE]-1'-CARBOXYLIC ACID, 1,2-DIHYDRO-, PHENYLMETHYL ESTER;benzylspiro[indoline-3,4'-piperidine]-1'-carboxylate;SCHEMBL1196005;SCHEMBL1196006;DTXSID201151979;MFCD06738866;AKOS015899319;AM85420;PB26234;AC-30834;AS-36230;B5847;CS-0049879;FT-0681898;EN300-201422;A810874;1'-benzyloxycarbonyl-spiro(indoline-3,4'-piperidine);Z1889856914;1'-(Benzyloxycarbonyl)spiro[1H-indole-3(2H),4'-piperidine];Phenylmethyl 1,2-dihydrospiro[3H-indole-3,4'-piperidine]-1'-carboxylate

Chemical Property of Benzyl spiro[indoline-3,4'-piperidine]-1'-carboxylate

Chemical Property:

• Melting Point: 118-120 °C
• Boiling Point: 505.157 °C at 760 mmHg
• PKA: 5.30±0.20(Predicted)
• Flash Point: 259.31 °C
• PSA: 41.57000
• Density: 1.237 g/cm³
• LogP: 3.85840
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 322.168127949
• Heavy Atom Count: 24
• Complexity: 439

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzyl Spiro[indoline-3,4'-piperidine]-1'-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC12CNC3=CC=CC=C23)C(=O)OCC4=CC=CC=C4

Technology Process of Benzyl spiro[indoline-3,4'-piperidine]-1'-carboxylate

There total 15 articles about Benzyl spiro[indoline-3,4'-piperidine]-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: 85.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + spiro[indoline-3,4′-piperidine] (171-75-5) → benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate (167484-18-6)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2004.03.081

Reference yield: 84.0%

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde (138163-08-3) + phenylhydrazine (100-63-0) → benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate (167484-18-6)

Guidance literature:

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde; phenylhydrazine; With trifluoroacetic acid; In toluene; acetonitrile; at 35 ℃;

With methanol; sodium tetrahydroborate; In toluene; acetonitrile; at 0 ℃; for 0.75h;

With ammonium hydroxide; In water; toluene; acetonitrile;

Reference yield:

4-fluorophenyhydrazine hydrochloride (823-85-8) + N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde (138163-08-3) → benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate (167484-18-6)

Guidance literature:

4-fluorophenyhydrazine hydrochloride; N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde; With trifluoroacetic acid; In toluene; acetonitrile; at 20 - 50 ℃;

With methanol; sodium tetrahydroborate; In toluene; acetonitrile; at 0 - 20 ℃;

With sodium hydrogencarbonate; In water; toluene; acetonitrile;

upstream raw materials:

benzyl spiro[indole-3,4'-piperidine]-1'-carboxylate

N-(Benzyloxycarbonyloxy)succinimide

spiro[indoline-3,4′-piperidine]

isonipecotic acid

Downstream raw materials:

1,2-dihydro-1-(2-nitrophenyl)-spiro[3H-indole-3,4'-piperidine]-1'-carboxylic acid phenylmethyl ester

1'-benzyl 1-methyl 1'H-spiro[indole-3,4'-piperidine]-1,1'(2H)-dicarboxylate

1'-benzyloxycarbonyl-1-tert-butyloxycarbonylspiro[indoline-3,4'-piperidine]

tert-butyl spiro[indoline-3,4'-piperidine]-1-carboxylate

Refernces

• 1、 -. "SUBSTITUTED HETEROCYCLIC DERIVATIVES AS GPR AGONISTS AND USES THEREOF". Page/Page column 86; 149; 150. . Retrieved 2015/03/16.
• 2、 Qi, Xian Liang,Yang, Er Qun,Zhang, Jun Tao,Wang, Tao,Cao, Xiao Ping. "A facile synthesis of the spiroindoline-based growth hormone secretagogue, MK-677". scheme or table. p. 661 - 664. Retrieved 2012/07/03.