Ammonium Hydroxide → (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexane-1-carboxamide

HRID 407528Notes

Reaction equation

HRID 407528 reaction equation
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[C:11](Cl)=[O:12])([CH3:3])[CH3:2].[OH-].[NH4+:15]>>[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[C:11]([NH2:15])=[O:12])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 3084750(1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbonyl chloride

Product 1

HCID 59253413(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexane-1-carboxamide

Procedure

A 250 mL flask was purged with nitrogen, left under a nitrogen atmosphere, and charged with 13.0 g (0.0641 mol) of (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbonyl chloride. While stirring 130 mL of 29% ammonium hydroxide solution was added to the flask. A white precipitate quickly formed, and after stirring overnight the fine white slurry was suction filtered. The filter cake was washed with water (3×50 mL) then dried in a vacuum oven (RT, 5 mm Hg, 3 days) to provide (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide as a white solid with the following spectroscopic properties.

Workup

  1. customA 250 mL flask was purged with nitrogen
  2. waitleft under a nitrogen atmosphere
  3. additionwas added to the flask
  4. customA white precipitate quickly formed
  5. filtrationfiltered
  6. washThe filter cake was washed with water (3×50 mL)
  7. customthen dried in a vacuum oven (RT, 5 mm Hg, 3 days)

Sources & evidence

ORD record
ord-500ac5beb60b499683e61902d6428adc
Source dataset
uspto-grants-2014_06
Patent number
US08754259B2

Reaction notes

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