Water → (4-(Methoxymethyl)cyclohexyl)methanamine

HRID 574964Notes

Reaction equation

HRID 574964 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]#[N:11])[CH2:6][CH2:5]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH2:11])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 671268194-(Methoxymethyl)cyclohexanecarbonitrile

Product 1

HCID 67126866(4-(Methoxymethyl)cyclohexyl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of EXAMPLE 374D (460 mg) in tetrahydrofuran (15 mL) was added 2M lithium aluminum hydride in tetrahydrofuran (2.252 mL) slowly. The reaction mixture was stirred at room temperature for 1 hour, refluxed for 1 hour and cooled. 2 ml of 2M aqueous NaOH and water (5 mL) was added. The solid was filtered off and washed with ether. The filtrate was concentrated. The residue was mixed with dichloromethane (50 mL) and the resulting mixture was dried over Na2SO4 and concentrated to provide the title compound.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperaturecooled
  3. filtrationThe solid was filtered off
  4. washwashed with ether
  5. concentrationThe filtrate was concentrated
  6. additionThe residue was mixed with dichloromethane (50 mL)
  7. dry with materialthe resulting mixture was dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ce1d17942c564c4fb6d2d1b785198c7a
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

Loading…