2-chloro-N-(2-chloroethyl)-N-[(5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methyl]ethanamine

Base Information

• Chemical Name: 2-chloro-N-(2-chloroethyl)-N-[(5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methyl]ethanamine
• CAS No.: 89651-52-5
• Molecular Formula: C₂₂H₂₃Cl₂N₃*ClH
• Molecular Weight: 436.812
• Mol file: 89651-52-5.mol

Synonyms:

Chemical Property of 2-chloro-N-(2-chloroethyl)-N-[(5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methyl]ethanamine

Chemical Property:

• Vapor Pressure: 1.63E-11mmHg at 25°C
• Boiling Point: 534.8°C at 760 mmHg
• Flash Point: 277.2°C
• Density: 1.26g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-chloro-N-(2-chloroethyl)-N-[(5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methyl]ethanamine

There total 13 articles about 2-chloro-N-(2-chloroethyl)-N-[(5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methyl]ethanamine 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: 60.0%

11-(bis-2-hydroxyethyl)amino-5,6-dimethylpyrido<4,3-b>carbazole (89651-50-3) → 11-(bis-2-chloroethyl)amino-5,6-dimethylpyrido<4,3-b>carbazole (HCl-salt) (89651-52-5)

Guidance literature:

With thionyl chloride; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88606-3

Reference yield:

1-methylindole (603-76-9) → 11-(bis-2-chloroethyl)amino-5,6-dimethylpyrido<4,3-b>carbazole (HCl-salt) (89651-52-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 63 percent / n-BuLi / tetrahydrofuran / 1 h

2: POCl₃ / pyridine / 1.) room temp, 1 h, 2:) 75 deg C, 1.5 h

3: NaBH₄ / ethanol / 2 h

4: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C

5: 2.) Et₃N / 1.) CH₃Cl, r.t.; 2.) EtOAc, r.t.

6: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature

7: 80 percent / H₂, NaHCO₃ / 10percent Pd-C / ethanol / 5 h / 760 Torr

8: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C

9: 58 percent / CH₂Cl₂ / 1 h / Ambient temperature

10: 77 percent / KOH / H₂O; ethane-1,2-diol / 160 - 170 °C

11: SOCl₂ / 2 h / Ambient temperature

12: 60 percent / acetonitrile / 0.5 h / Heating

13: 60 percent / SOCl₂ / 20 h / Ambient temperature

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; thionyl chloride; hydrogen; 10-benzylacridin-10-ium bromide; sodium hydrogencarbonate; triethylamine; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; pyridine; sulfolane; ethanol; dichloromethane; water; ethylene glycol; acetonitrile;

DOI:10.1016/S0040-4020(01)88606-3

Reference yield:

Ethyl α-(N-methylindol-2-yl)acrylate (72938-66-0) → 11-(bis-2-chloroethyl)amino-5,6-dimethylpyrido<4,3-b>carbazole (HCl-salt) (89651-52-5)

Guidance literature:

Multi-step reaction with 11 steps

1: NaBH₄ / ethanol / 2 h

2: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C

3: 2.) Et₃N / 1.) CH₃Cl, r.t.; 2.) EtOAc, r.t.

4: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature

5: 80 percent / H₂, NaHCO₃ / 10percent Pd-C / ethanol / 5 h / 760 Torr

6: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C

7: 58 percent / CH₂Cl₂ / 1 h / Ambient temperature

8: 77 percent / KOH / H₂O; ethane-1,2-diol / 160 - 170 °C

9: SOCl₂ / 2 h / Ambient temperature

10: 60 percent / acetonitrile / 0.5 h / Heating

11: 60 percent / SOCl₂ / 20 h / Ambient temperature

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; thionyl chloride; hydrogen; 10-benzylacridin-10-ium bromide; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; sulfolane; ethanol; dichloromethane; water; ethylene glycol; acetonitrile;

DOI:10.1016/S0040-4020(01)88606-3

upstream raw materials:

11-(bis-2-hydroxyethyl)amino-5,6-dimethylpyrido<4,3-b>carbazole

1-methylindole

Ethyl α-(N-methylindol-2-yl)acrylate

ethyl 2-(1-methyl-1H-indol-2-yl)propanoate