Borane;tetrahydrofuran → [6-(cyclohexyloxy)pyridin-3-yl]methylamine

HRID 1190970Notes

Reaction equation

HRID 1190970 reaction equation
[CH:1]1([O:7][C:8]2[N:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.C1COCC1>C1COCC1>[NH2:15][CH2:14][C:11]1[CH:12]=[N:13][C:8]([O:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 24698739HCID 24698739, compound

Product 1

HCID 16781318[6-(cyclohexyloxy)pyridin-3-yl]methylamineYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 6-cyclohexyloxy-pyridine-3-carbonitrile (1 g, 5 mmol) in anhydrous THF (7 mL) under nitrogen and cool the mixture at 0° C. Add borane-THF complex (15 mL, 15 mmol, 1M solution in THF) and stir the reaction mixture at room temperature overnight. Pour slowly the reaction mixture into an ice-cold 5N aqueous HCl (50 mL) and stir the resulting solution for 4 h. Concentrate in vacuo, take up the resulting solid with a minimum amount of methanol and filter through a SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound as a yellow oil (621 mg, 62%). MS (ES+) m/z: 207 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. filtrationfilter through a SCX-2 column
  3. washeluting with methanol

Sources & evidence

ORD record
ord-071ad31169d84faba140ae5a85d22b05
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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