4-(Aminomethyl)tetrahydro-2H-pyran Chemical Properties

Boiling point:

75 °C

Density 

1.02

refractive index 

1.4630-1.4670

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

clear liquid

pka

10.01±0.29(Predicted)

color 

Colorless to Light yellow

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 Information

Hazard Codes 

Xi,C,Xn

Risk Statements 

34-41-37/38-22

Safety Statements 

26-36/37/39-45-39

RIDADR 

2735

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29329990

4-(Aminomethyl)tetrahydro-2H-pyran Usage And Synthesis

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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