| Identification | Back Directory | [Name]
1-N-Boc-5-oxo-1,4-diazepane | [CAS]
190900-21-1 | [Synonyms]
ic Acid Tert-ButyL
N-Boc-1,4-diazepan-5-one
1-Boc-1,4-diazepan-5-one
N1-BOC-5-oxo-1,4-diazepane
1-N-Boc-5-oxo-1,4-Diazepane
5-Oxo-[1,4]Diazepane-1-CarboxyL
1,4-Diazepan-5-one, N1-Boc protected
Homopiperazin-5-one, N1-BOC protected
tert-Butyl-5-oxo-1,4-diazepan-1-carboxylat
5-Oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester
1H-1,4-diazepine-1-carboxylic acid, hexahydro-5-oxo-, 1,1- | [Molecular Formula]
C10H18N2O3 | [MDL Number]
MFCD04115319 | [MOL File]
190900-21-1.mol | [Molecular Weight]
214.26 |
| Chemical Properties | Back Directory | [Boiling point ]
373.1±35.0 °C(Predicted) | [density ]
1.098±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
16.06±0.20(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C10H18N2O3/c1-10(2,3)15-9(14)12-6-4-8(13)11-5-7-12/h4-7H2,1-3H3,(H,11,13) | [InChIKey]
GLJYPTWEXBUATJ-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CCC(=O)NCC1 |
| Hazard Information | Back Directory | [Uses]
1-N-Boc-5-oxo-1,4-diazepane is a 1,4-diazepane derivatives compound，used as sigma receptor ligands in antipsychotics, antiamnesics, and against other neurodegenerative disorders as well as neuroprotective agents.[1] | [Synthesis]
The general procedure for the synthesis of N-Boc-1,4-diaza-5-cycloheptanone from 4-oxime-1-Boc-piperidine was as follows: to a solution of tetrahydrofuran (THF, 10 mL) containing the ketoxime (0.01 mol) was added T3P (15 mol%, 50% solution in ethyl acetate). The reaction mixture was stirred at reflux for 1-4 h under nitrogen protection. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the solvent was removed under reduced pressure. The residue was diluted with distilled water (20 mL) and subsequently extracted with ethyl acetate (2 x 20 mL). The organic phases were combined and washed sequentially with saturated sodium bicarbonate (NaHCO3) solution (1 × 10 mL) and brine. The organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give a high purity target amide product. | [References]
[1] Daniele Zampieri*. “Synthesis, Cytotoxicity Evaluation, and Computational Insights of Novel 1,4-Diazepane-Based Sigma Ligands.” ACS Medicinal Chemistry Letters 11 5 (2019): 651–656. |
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