1-Benzyl-1,4-diazepan-5-one Chemical Properties

Melting point:

115-117°

Boiling point:

379.8±35.0 °C(Predicted)

Density 

1.097±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

16.00±0.20(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2914290090

1-Benzyl-1,4-diazepan-5-one Usage And Synthesis

Uses

1-Benzyl-1,4-diazepan-5-one is a diazepane intermediate that can be used as an inhibitor of human nitric oxide synthesis.

Synthesis

General procedure for the synthesis of 1-benzyl-1,4-diazepan-5-one from N-benzylpiperidone: [Ref. Example 119]; 1-benzylhexahydro-1H-1,4-diazepan-5-one; [] Concentrated sulfuric acid (25 mL) was slowly added dropwise to a solution of acetic acid (50 mL) of 1-benzyl-4-piperidone (10.14 g) at room temperature followed by a batch at 0 °C Sodium azide (3.880 g) was added. The reaction was carried out at 0 °C for 2 h, followed by warming to 5 °C and stirring for 25 h. The reaction was completed with the addition of sodium hydroxide (3.880 g). Upon completion of the reaction, the reaction mixture was adjusted to alkaline with aqueous sodium hydroxide solution followed by liquid-liquid partition extraction with chloroform. The aqueous layer was further extracted with chloroform. All organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed by concentration under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform-methanol gradient) to afford 1-benzyl-1,4-diazepan-5-one as a white solid (5.081 g, 47% yield).1H-NMR (400 MHz, CDCl3) δ: 2.50-2.70 (6H, m), 3.20-3.35 (2H, m) , 3.60 (2H, s), 6.07 (1H, br), 7.20-7.40 (5H, m).MS (ESI) m/z: 205 (M + H)+.

References

[1] Patent: EP1591443, 2005, A1. Location in patent: Page/Page column 72
[2] Tetrahedron Letters, 1991, vol. 32, # 22, p. 2469 - 2470
[3] Patent: WO2012/101654, 2012, A2
[4] Patent: WO2014/16849, 2014, A2

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• 1-(3-METHOXYBENZYL)-4-(PYRIDIN-2-YLMETHYL)-1,4-DIAZEPAN-5-ONE
• 4-[2-(DIFLUOROMETHOXY)BENZYL]-1-[4-(METHYLSULFONYL)BENZYL]-1,4-DIAZEPAN-5-ONE
• 3-((4-[2-(4-FLUOROPHENOXY)ETHYL]-5-OXO-1,4-DIAZEPAN-1-YL)METHYL)BENZONITRILE
• 4-[2-(DIFLUOROMETHOXY)BENZYL]-1-(3-METHOXYBENZYL)-1,4-DIAZEPAN-5-ONE
• 4-(3,5-DIMETHOXYBENZYL)-1-(3-METHOXYBENZYL)-1,4-DIAZEPAN-5-ONE
• 4-(BIPHENYL-2-YLMETHYL)-1-(3-METHOXYBENZYL)-1,4-DIAZEPAN-5-ONE