Cyclohexanone cyanohydrin → 1-(Aminomethyl)cyclohexan-1-ol

HRID 1848055Notes

Reaction equation

HRID 1848055 reaction equation
[CH2:1]1[CH2:6][CH2:5][C:4]([OH:9])([C:7]#[N:8])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1.C(Cl)Cl.O>[NH2:8][CH2:7][C:4]1([OH:9])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 13610Cyclohexanone cyanohydrinHCID 14798Sodium HydroxideHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 776141-(Aminomethyl)cyclohexan-1-olYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of cyclohexanone cyanohydrin (2 g, 15.98 mmol) in anhydrous THF (40 mL) at rt was added portion-wise LiAlH4 (1.82 g, 47.94 mmol). The reaction vessel was sealed and the mixture was heated at 80° C. for 5 h. The mixture was cooled to 0° C. and water (1 mL), 1M aq NaOH (1 mL), and water (3 mL) were added sequentially. To the resulting mixture was added DCM and saturated aq sodium potassium tartrate, and the mixture stirred for 3 h. The organic layer was separated and further washed with brine. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure to afford 1-(aminomethyl)cyclohexanol (1.3 g) which was not purified further. LCMS (ESI) m/z 130 (M+H)+.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe mixture was cooled to 0° C.
  3. customThe organic layer was separated
  4. washfurther washed with brine
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40624138851845909fd8916131d4fe0b
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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