3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane

Base Information

• Chemical Name: 3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane
• CAS No.: 1259556-07-4
• Molecular Formula: C₁₈H₂₆N₂O₂
• Molecular Weight: 302.417
• Mol file: 1259556-07-4.mol

Synonyms:3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane

Chemical Property of 3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane

There total 7 articles about 3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane 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: 37.0%

2-chloroethyl methyl ether (627-42-9) + dihydrochloride salt of 1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane → 3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane (1259556-07-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100 ℃; for 16h;

Reference yield:

4-Bromophenylacetonitrile (16532-79-9) → 3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane (1259556-07-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -10 °C

1.2: 4 h / -10 - 20 °C

2.1: dimethylsulfide borane complex; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 80 °C

2.2: 0 °C

2.3: pH 8

3.1: thionyl chloride / 1,1-dichloroethane / 2 h / 0 - 20 °C

3.2: 0 °C / pH 8

4.1: triethylamine / dichloromethane / 2 h / 0 °C

5.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 4 h / 20 - 90 °C

6.1: hydrogenchloride / diethyl ether

7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 - 100 °C

With hydrogenchloride; thionyl chloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; N-ethyl-N,N-diisopropylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; 1,1-dichloroethane; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane (86215-40-9) → 3-(2-methoxy-ethyl)-1-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane (1259556-07-4)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 2 h / 0 °C

2: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 4 h / 20 - 90 °C

3: hydrogenchloride / diethyl ether

4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 - 100 °C

With hydrogenchloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; N-ethyl-N,N-diisopropylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

2-chloroethyl methyl ether

4-Bromophenylacetonitrile

1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane

tert-butyl 1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate