(R)-5-(2-Aminopropyl)-1-(3-(benzyloxy)propyl)indoline-7-carbonitrile

Base Information

• Chemical Name: (R)-5-(2-Aminopropyl)-1-(3-(benzyloxy)propyl)indoline-7-carbonitrile
• CAS No.: 459868-73-6
• Molecular Formula: C22H27N3O
• Molecular Weight: 349.476
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50432615
• Wikidata: Q72441271
• Mol file: 459868-73-6.mol

Synonyms:459868-73-6;(R)-5-(2-Aminopropyl)-1-(3-(benzyloxy)propyl)indoline-7-carbonitrile;5-[(2R)-2-AMINOPROPYL]-2,3-DIHYDRO-1-[3-(PHENYLMETHOXY)PROPYL]-1H-INDOLE-7-CARBONITRILE;5-[(2R)-2-aminopropyl]-1-(3-phenylmethoxypropyl)-2,3-dihydroindole-7-carbonitrile;5-[(2R)-2-Aminopropyl]-1-[3-(benzyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile;5-((2r)-2-aminopropyl)-2,3-dihydro-1-(3-(phenylmethoxy)propyl)-1h-indole-7-carbonitrile;SCHEMBL12247877;DTXSID50432615;(R)-5-(2-Aminopropyl)-1-(3-benzyloxypropyl)indoline-7-carbonitrile;AKOS016007588;AC-23951;5-[(2R)-2-Aminopropyl]-1-[3-(benzyloxy)propyl]-7-indolinecarbonitrile

Chemical Property of (R)-5-(2-Aminopropyl)-1-(3-(benzyloxy)propyl)indoline-7-carbonitrile

Chemical Property:

• Boiling Point: 539.31 °C at 760 mmHg
• PKA: 9.65±0.10(Predicted)
• Flash Point: 279.965 °C
• PSA: 62.28000
• Density: 1.15 g/cm³
• LogP: 4.18268
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 349.215412493
• Heavy Atom Count: 26
• Complexity: 467

Purity/Quality:

99% ^*data from raw suppliers

(R)-5-(2-Aminopropyl)-1-(3-(benzyloxy)propyl)indoline-7-carbonitrile 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC2=C(C(=C1)C#N)N(CC2)CCCOCC3=CC=CC=C3)N
• Isomeric SMILES: C[C@H](CC1=CC2=C(C(=C1)C#N)N(CC2)CCCOCC3=CC=CC=C3)N

Technology Process of (R)-5-(2-Aminopropyl)-1-(3-(benzyloxy)propyl)indoline-7-carbonitrile

There total 10 articles about (R)-5-(2-Aminopropyl)-1-(3-(benzyloxy)propyl)indoline-7-carbonitrile 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:

C30H33N3O3 (900518-68-5) → C22H27N3O (459868-73-6)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 3h; under 11251.1 Torr;

DOI:10.1016/j.tetlet.2013.01.003

Reference yield:

1-indoline (496-15-1) → C22H27N3O (459868-73-6)

Guidance literature:

Multi-step reaction with 10 steps

1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 3.5 h / 100 °C

2: trichlorophosphate / 4 h / 25 - 35 °C

3: bromine / dichloromethane / 2.5 h / 0 °C

4: dichloromethane; toluene / 16 h / Reflux

5: sodium hydroxide / methanol; water / 3 h / 40 °C

6: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / Autoclave; Inert atmosphere

7: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C

8: 10 h / 95 °C

9: N,N-dimethyl-formamide / 20 h / 120 °C / Inert atmosphere

10: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr

With diphenyl phosphoryl azide; palladium on activated charcoal; hydrogen; bromine; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; sodium hydroxide; trichlorophosphate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: |Vilsmeier-Haack Formylation / 4: |Wittig Olefination;

DOI:10.1016/j.tetlet.2013.01.003

Reference yield:

C22H25BrN2O2 → C22H27N3O (459868-73-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 10 h / 95 °C

2: N,N-dimethyl-formamide / 20 h / 120 °C / Inert atmosphere

3: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr

With palladium on activated charcoal; hydrogen; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2013.01.003

upstream raw materials:

C₃₀H₃₃N₃O₃

1-indoline

1-chloro-3-benzyloxypropane

1-[3-(benzyloxy)propyl]indoline

Downstream raw materials:

tert-butyl (2R)-(1-(1-(3-benzyloxypropyl)-7-cyanoindolin-5-yl)propane-2-yl)-N-(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)carbamate

tert-butyl (2R)-(1-(1-(3-benzyloxypropyl)-7-carbamoylindolin-5-yl)propan-2-yl)-N-(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)carbamate

silodosin

2,3-dihydro-1-[3-(phenylmethoxy)propyl]-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

Refernces