Water → (4-(Methoxymethyl)cyclohexyl)methanamine

HRID 573228Notes

Reaction equation

HRID 573228 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

Procedure

To a solution of EXAMPLE 454D (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. Sodium hydroxide (2 ml of 2M solution) 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 Na2CO3, filtered, 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 Na2CO3
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b16a953cc600465c8b370b363fd502ff
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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