2-Morpholinemethanamine, 4-[(4-fluorophenyl)methyl]-, (2S)-

Base Information

• Chemical Name: 2-Morpholinemethanamine, 4-[(4-fluorophenyl)methyl]-, (2S)-
• CAS No.: 156334-89-3
• Molecular Formula: C12H17FN2O
• Molecular Weight: 224.278
• Mol file: 156334-89-3.mol

Synonyms:2-Morpholinemethanamine, 4-[(4-fluorophenyl)methyl]-, (S)-;

Chemical Property of 2-Morpholinemethanamine, 4-[(4-fluorophenyl)methyl]-, (2S)-

Chemical Property:

• Boiling Point: 317.4±27.0 °C(Predicted)
• PKA: 9.37±0.29(Predicted)
• PSA: 38.49000
• Density: 1.145±0.06 g/cm3(Predicted)
• LogP: 1.62340

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Morpholinemethanamine, 4-[(4-fluorophenyl)methyl]-, (2S)-

There total 16 articles about 2-Morpholinemethanamine, 4-[(4-fluorophenyl)methyl]-, (2S)- 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:

(S)-2-(azidomethyl)-4-(4-fluorobenzyl)morpholine → (S)-(-)-<4-(4-fluorobenzyl)-2-morpholinyl>methylamine (156334-89-3)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at -5 - 20 ℃; for 1.5h; Yield given;

DOI:10.1248/cpb.42.877

Reference yield:

(2R)-2-[(benzyloxy)methyl]morpholine (135065-70-2) → (S)-(-)-<4-(4-fluorobenzyl)-2-morpholinyl>methylamine (156334-89-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 3 g / hydrogen / palladium-on-carbon / ethanol / 50 °C

2: NaI, K₂CO₃ / butan-2-one / 18 h / Heating

3: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.) 5 deg C, 2.) RT, 24 h

4: 2.1 g / sodium azide / dimethylformamide / 2 h / 120 °C

5: 70percent sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 1.5 h / -5 - 20 °C

With dmap; sodium azide; hydrogen; potassium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; butanone;

DOI:10.1248/cpb.42.877

Reference yield:

para-fluorobenzylamine (140-75-0) → (S)-(-)-<4-(4-fluorobenzyl)-2-morpholinyl>methylamine (156334-89-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / cyclohexane / 16 h / Ambient temperature

2: 84 percent / CHCl₃ / 1 h / Ambient temperature

3: 60 percent / MeONa / methanol / 3 h / Heating

4: 81 percent / BF₃*THF / tetrahydrofuran / 4 h / Heating

5: 75 percent / dimethylformamide / 5 h / Ambient temperature

6: 8.4 g / 85percent hydrazine hydrate / ethanol / 0.5 h / Heating

With boron trifluoride-tetrahydrofuran complex; sodium methylate; hydrazine hydrate; In tetrahydrofuran; methanol; ethanol; chloroform; cyclohexane; N,N-dimethyl-formamide;

upstream raw materials:

(R)-(-)-N-<<4-(4-fluorobenzyl)-2-morpholinyl>methyl>phthalimide

2-(4-fluoro-benzyl-amino)-ethanol

4-fluorobenzaldehyde

(2R)-2-[(benzyloxy)methyl]morpholine

Refernces

• 1、 Morie, Toshiya,Kato, Shiro,Harada, Hiroshi,Matsumoto, Jun-ichi. "ASYMMETRIC SYNTHESIS OF THE ENANTIOMERS OF 2-AMINOMETHYL-4-(4-FLUOROBENZYL)MORPHOLINE, AN INTERMEDIATE OF MOSAPRIDE, A GASTROPROKINETIC AGENT". . p. 1033 - 1040. Retrieved 2007/10/02.