(S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane

Base Information

• Chemical Name: (S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane
• CAS No.: 113997-59-4
• Molecular Formula: C₁₉H₂₂N₂
• Molecular Weight: 278.397
• Mol file: 113997-59-4.mol

Synonyms:(S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane

Chemical Property of (S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane

There total 3 articles about (S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane 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: 36.0%

3-(1H-indolyl)acetone (1201-26-9) + (S)-1-phenyl-ethylamine (2627-86-3) → (S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane (113997-59-4) + (S,R)-N-α-phenetyl-1-indol-3-yl-2-aminopropane (113997-61-8)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; for 24h; Ambient temperature; pH 5 - 6;

DOI:10.1021/jm00402a026

Reference yield:

3-(1H-indolyl)acetone (1201-26-9) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane (113997-59-4) + (R)-1-(1H-indol-3-yl)-N-((R)-1-phenylethyl)propan-2-amine (113997-58-3)

Guidance literature:

3-(1H-indolyl)acetone; (R)-1-phenyl-ethyl-amine; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In dichloromethane; at 0 - 20 ℃; for 20.5h; Overall yield = 29.6 percent; Overall yield = 11.91 g; Inert atmosphere;

Reference yield:

α-methyl-β-(3-indolyl)-1-nitroethane (4771-72-6) → (S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane (113997-59-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOCH₃, 2.) aq. TiCl₃, aq. AcONH₄ / 1) CH₃OH, 30 min, room temperature; 2) room temperature, 12 h

2: 54 percent / NaBH₃CN, glacial acetic acid / methanol / 24 h / Ambient temperature; pH 5 - 6

With titanium(III) chloride; ammonium acetate; sodium methylate; sodium cyanoborohydride; acetic acid; In methanol;

DOI:10.1021/jm00402a026

upstream raw materials:

3-(1H-indolyl)acetone

(S)-1-phenyl-ethylamine

α-methyl-β-(3-indolyl)-1-nitroethane

(R)-1-phenyl-ethyl-amine

Downstream raw materials:

(+)-alpha-Methyltryptamine

Refernces

• 1、 Nichols,Lloyd,Johnson,Hoffman. "Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: Evidence for the binding conformation of tryptamines at serotonin 5-HT(1B) receptors". . p. 1406 - 1412. Retrieved 2007/10/02.