Water → (4-(Methoxymethyl)cyclohexyl)methanamine

HRID 2168148Notes

Reaction equation

HRID 2168148 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-528854c218de42cfa0256fee6f2e39e0
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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