| Identification | Back Directory | [Name]
1-(CYCLOPROPYLMETHYL)PIPERAZINE 97 | [CAS]
57184-25-5 | [Synonyms]
Cyclopropylmethyl-piperazin-1-
N-(Cyclopropylmethyl)piperazine
1-(CYCLOPROPYLMETHYL)PIPERAZINE 97
[(Piperazin-1-yl)methyl]cyclopropane
1-(cyclopropylmethyl)piperazine(SALTDATA: FREE)
1-(Cyclopropylmethyl)piperazine, 97%
colorless to yellow liquid | [Molecular Formula]
C8H16N2 | [MDL Number]
MFCD00872053 | [MOL File]
57184-25-5.mol | [Molecular Weight]
140.228 |
| Chemical Properties | Back Directory | [Boiling point ]
68 °C3.5 mm Hg
| [density ]
0.943 g/mL at 25 °C
| [refractive index ]
n20/D 1.489
| [Fp ]
171 °F
| [storage temp. ]
2-8°C | [form ]
liquid | [pka]
9.25±0.10(Predicted) | [color ]
Light brown | [InChI]
InChI=1S/C8H16N2/c1-2-8(1)7-10-5-3-9-4-6-10/h8-9H,1-7H2 | [InChIKey]
IVLIBVDZIYFXBZ-UHFFFAOYSA-N | [SMILES]
N1(CC2CC2)CCNCC1 | [CAS DataBase Reference]
57184-25-5 |
| Hazard Information | Back Directory | [Uses]
1-(Cyclopropylmethyl)piperazine is a compound involved in the preparation of N-substituted piperazinopyridylsteroid derivatives as abiraterone analogs that inhibit growth and induce pro-apoptosis in human hormone-independent prostate cancer cell lines. | [Synthesis]
S3: In a 10L four-necked flask equipped with a mechanical stirrer and a thermometer, N-Boc-4-(cyclopropylmethyl)piperazine (2.00 kg, 8.32 mol) and 5 kg of isopropanol were added and heated up to 40 °C. Concentrated hydrochloric acid (2.04 kg, 20.80 mol) was slowly added dropwise, and the reaction temperature was controlled between 40°C and 50°C. After the dropwise addition, the reaction was maintained at 40°C to 50°C with stirring for 4 hours. Upon completion of the reaction, the reaction solution was concentrated to remove most of the isopropanol and cooled to 0 °C. The pH of the residue was adjusted to 10-11 with 5 mol/L aqueous sodium hydroxide. extraction was carried out with dichloromethane (5L x 3), the organic phases were combined and washed once with 5 kg of saturated aqueous sodium chloride. The organic phase was diluted with dichloromethane to give 1.11 kg of a light yellow liquid 1-cyclopropylmethylpiperazine in 94% yield. The NMR spectrum of the product was consistent with the standard spectrum. | [References]
[1] Patent: CN108341792, 2018, A. Location in patent: Paragraph 0030; 0035
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 11, p. 2833 - 2838
[3] Patent: EP2481739, 2012, A1. Location in patent: Page/Page column 68
[4] Patent: WO2018/5860, 2018, A1. Location in patent: Page/Page column 172; 201; 203 |
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