4-chlorogramine

Base Information

• Chemical Name: 4-chlorogramine
• CAS No.: 40247-57-2
• Molecular Formula: C11H13ClN2
• Molecular Weight: 208.691
• Hs Code.: 2933990090
• Mol file: 40247-57-2.mol

Synonyms:4-CHLOROGRAMINE

Chemical Property of 4-chlorogramine

Chemical Property:

• Melting Point: 147.6-148.4 °C(Solv: acetone (67-64-1))
• Boiling Point: 327.4±27.0 °C(Predicted)
• PKA: 16.10±0.30(Predicted)
• PSA: 19.03000
• Density: 1.224±0.06 g/cm3(Predicted)
• LogP: 2.88290

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-chlorogramine

There total 13 articles about 4-chlorogramine 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: 78.0%

N-{[4-chloro-1-(1,1,1-triisopropylsilyl)-1H-3-indolyl]methyl}-N,N-dimethylamine (146886-60-4) → 4-chloro-3-dimethylaminomethylindole (40247-57-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.166667h; Ambient temperature;

DOI:10.3987/COM-92-6185

Reference yield: 59.9%

4-chloro-1H-indole (25235-85-2) + N,N-dimethyl(methylene)ammonium chloride (30354-18-8) → 4-chloro-3-dimethylaminomethylindole (40247-57-2)

Guidance literature:

In acetonitrile; for 18h; Ambient temperature;

DOI:10.1248/cpb.29.3145

Reference yield:

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine (146886-51-3) → 4-chloro-3-dimethylaminomethylindole (40247-57-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuLi / diethyl ether; pentane / 1 h / 0 °C

1.2: 64 percent / Cl₃CCCl₃ / tetrahydrofuran; diethyl ether; pentane / 5 h / -78 - 20 °C

2.1: TBAF / tetrahydrofuran / 0.17 h / 20 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane;

DOI:10.1021/ol017310m

upstream raw materials:

4-chloro-1H-indole

N,N-dimethyl(methylene)ammonium chloride

N-{[4-chloro-1-(1,1,1-triisopropylsilyl)-1H-3-indolyl]methyl}-N,N-dimethylamine

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine

Downstream raw materials:

4-chloroindole-3-acetic acid

4-chloro-DL-tryptophan

tert-butyl 4-chloro-3-iodo-1H-indolecarboxylate

Refernces

• 1、 -. "Tryptamine analogues, their synthesis and their use as 5-HT1 -like or 5-HT2 receptor agonists". . . Retrieved 2008/06/13.
• 2、 Somei,Tsuchiya. "The chemistry of indoles. XVI. A convenient synthesis of substituted indoles carrying a hydroxy group, a halogeno group, or a carbon side chain at the 4-position via 4-indolediazonium salts and a total synthesis of (±)-6,7-secoagroclavine". . p. 3145 - 3157. Retrieved 2007/10/02.