3-AMINO-1-METHYL-5-PHENYL-1,3-DIHYDRO-BENZO[E][1,4]DIAZEPIN-2-ONE

Base Information

• Chemical Name: 3-AMINO-1-METHYL-5-PHENYL-1,3-DIHYDRO-BENZO[E][1,4]DIAZEPIN-2-ONE
• CAS No.: 103343-65-3
• Molecular Formula: C16H15 N3 O
• Molecular Weight: 265.315
• Hs Code.: 2933990090
• Mol file: 103343-65-3.mol

Synonyms:2H-1,4-Benzodiazepin-2-one,3-amino-1,3-dihydro-1-methyl-5-phenyl-, (R)-; (R)-3-Amino-1-methyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

Chemical Property of 3-AMINO-1-METHYL-5-PHENYL-1,3-DIHYDRO-BENZO[E][1,4]DIAZEPIN-2-ONE

Chemical Property:

• PSA: 58.69000
• LogP: 1.98610

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-AMINO-1-METHYL-5-PHENYL-1,3-DIHYDRO-BENZO[E][1,4]DIAZEPIN-2-ONE

There total 21 articles about 3-AMINO-1-METHYL-5-PHENYL-1,3-DIHYDRO-BENZO[E][1,4]DIAZEPIN-2-ONE 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:

3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (103421-61-0) → (S)-3-amino-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one (103343-66-4) + (3R)-3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (103343-65-3)

Guidance literature:

With CHIRALPAK AS-H; In methanol; carbon dioxide; diethylamine; at 35 ℃; under 75007.5 Torr; Purification / work up; Resolution of racemate;

Reference yield:

3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (103421-61-0) → (3R)-3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (103343-65-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 g / 1-hydroxybenzotriazole, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, triethylamine / dimethylformamide / 0.25 h / pH = 9.5

2: HCl(g) / ethyl acetate / 0.5 h / 0 °C

3: 1) PhCNS; 2) CF₃CO₂H / 1) CH₂Cl₂, reflux, 20 min; 2) 50 deg C, 20 min

With hydrogenchloride; benzonitrile sulphide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00391a010

Reference yield:

2'-benzoyl-2-bromo-acetanilide (14439-71-5) → (3R)-3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (103343-65-3)

Guidance literature:

Multi-step reaction with 7 steps

1: NH₃ / methanol / 2 h / Heating

2: 93 percent / Aliquat 336, 50percent aq. NaOH / toluene / 4 h / 20 - 25 °C

3: 81.6 percent / t-BuOK, isoamyl nitrite / toluene / 0.5 h / -20 - 0 °C

4: H₂ / 5percent Ru/C / methanol / 24 h / 68 - 74 °C / 2068.6 Torr

5: 90 g / 1-hydroxybenzotriazole, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, triethylamine / dimethylformamide / 0.25 h / pH = 9.5

6: HCl(g) / ethyl acetate / 0.5 h / 0 °C

7: 1) PhCNS; 2) CF₃CO₂H / 1) CH₂Cl₂, reflux, 20 min; 2) 50 deg C, 20 min

With hydrogenchloride; sodium hydroxide; benzonitrile sulphide; potassium tert-butylate; ammonia; hydrogen; Aliquat 336; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; isopentyl nitrite; Ru-carbon; In methanol; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00391a010

upstream raw materials:

(R)-2-Amino-N-((R)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-3-phenyl-propionamide

(S)-2-Amino-N-((R)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-3-phenyl-propionamide

(R)-α-amino-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)benzenepropanamide

2'-benzoyl-2-bromo-acetanilide

Downstream raw materials:

(R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-4-pentylbenzamide

2-Chloro-N-((R)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-benzamide

(+)-N-[(3R)-2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzo-diazepin-3-yl]cyclohexylcarboxamide