Identification | More | [Name]
4-(Aminomethyl)tetrahydro-2H-pyran | [CAS]
130290-79-8 | [Synonyms]
1-TETRAHYDRO-2H-PYRAN-4-YLMETHANAMINE 4-AMINOMETHYLTETRAHYDROPYRAN ASINEX-REAG BAS 07731534 C-(TETRAHYDRO-PYRAN-4-YL)-METHYLAMINE (TETRAHYDRO-2H-PYRAN-4-YL) METHANAMINE (TETRAHYDRO-2H-PYRAN-4-YLMETHYL)AMINE (TETRAHYDROPYRAN-4-YL)METHYLAMINE 4-(Aminomethyl)tetrahydropyrane 4-AMINOMETYYLTETRAHYDROPYRAN 4-(Aminomethyl)tetrahydro-2H-pyran 4-Aminomethyltetrahydropyran ,97% | [EINECS(EC#)]
638-888-2 | [Molecular Formula]
C6H13NO | [MDL Number]
MFCD02179435 | [Molecular Weight]
115.17 | [MOL File]
130290-79-8.mol |
Chemical Properties | Back Directory | [Appearance]
clear colorless liquid | [Boiling point ]
75 °C | [density ]
1.02 | [refractive index ]
1.4630-1.4670 | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
clear liquid | [pka]
10.01±0.29(Predicted) | [color ]
Colorless to Light yellow | [Detection Methods]
GC,NMR | [InChI]
InChI=1S/C6H13NO/c7-5-6-1-3-8-4-2-6/h6H,1-5,7H2 | [InChIKey]
IPBPLHNLRKRLPJ-UHFFFAOYSA-N | [SMILES]
C1OCCC(CN)C1 | [CAS DataBase Reference]
130290-79-8(CAS DataBase Reference) |
Safety Data | Back Directory | [Hazard Codes ]
Xi,C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
2735 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [PackingGroup ]
Ⅲ | [HS Code ]
29329990 |
Hazard Information | Back Directory | [Chemical Properties]
clear colorless liquid | [Uses]
4-Aminomethyltetrahydropyran is a reagent that is used in core modification in discovery of CC214-2 which is an orally available , selective inhibitor of mTOR kinase. 4-Aminomethyltetrahydropyran is also used as a reagent in the development of pyrazoloquinolines as PDE10A inhibitor for the treatment of schizophrenia. | [Synthesis]
Example 43 (Synthesis of 4-aminomethyltetrahydropyran): In a 200 mL stainless steel autoclave equipped with a stirring device, a thermometer, and a manometer, 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 50.0 g of a 22% (w/w) ammonia-methanol solution, and 2.0 g (17.0 mmol as nickel atoms) of activated Raney nickel ( provided by Nikki Chemical Co., Ltd; nickel sponge N154D). The reaction was stirred under hydrogen atmosphere at 45 to 55 °C and 0.51 to 0.61 MPa pressure for 17 hours. After completion of the reaction, the insoluble material was removed by filtration and the filtrate was washed with 30 mL of methanol. The filtrate and washings were combined, concentrated under reduced pressure and then distilled under reduced pressure at 73-74 °C and 2.67 kPa to give 7.94 g (76.6% isolated yield) of 4-aminomethyltetrahydropyran as a colorless liquid. Its physical properties were as follows: 1H-NMR (DMSO-d6, δ (ppm)): 1.02-1.16 (2H, m), 1.10-1.50 (2H, brs), 1.34-1.45 (1H, m), 1.56-1.61 (2H, m), 2.39 (2H, d, J = 6.3 Hz), 3.20-3.29 (2H, m ), 3.81-3.86 (2H, m); CI-MS (m/e): 116 (M+1), 99.
Example 45 (Synthesis of 4-aminomethyltetrahydropyran): in a 200 mL stainless steel autoclave equipped with a stirring device, a thermometer, and a manometer, 10.0 g (90.0 mmol) of 4-cyanotetrahydropyran, 100 mL of a 22% (w/w) ammonia-methanol solution, and 2.0 g (17.0 mmol as nickel atoms) of activated Raney nickel ( provided by Nikki Chemical Co., Ltd; nickel sponge N154D). The reaction was stirred under hydrogen atmosphere at 50 to 60 °C and 0.51 to 0.61 MPa pressure for 5 hours. After completion of the reaction, the insoluble material was removed by filtration and the filtrate was washed with 30 mL of methanol. The filtrate and washings were combined and analyzed by gas chromatography (internal standard method) to confirm the formation of 8.84 g (85.3% reaction yield) of 4-aminomethyltetrahydropyran and no by-product bis(4-tetrahydropyranosylmethyl)amine was detected. | [References]
[1] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 16-17 [2] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 17 [3] Justus Liebigs Annalen der Chemie, 1938, vol. 535, p. 37,45 [4] Patent: US6372778, 2002, B1. Location in patent: Example 80 [5] Patent: US2006/63804, 2006, A1. Location in patent: Page/Page column 13 |
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