Cyclohexanecarboxylic acid → Cyclohexanecarboxamide

HRID 1049327Notes

Reaction equation

HRID 1049327 reaction equation
[CH:1]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1N=C[N:12](C(N2C=NC=C2)=O)C=1.[OH-].[NH4+]>CCOC(C)=O>[CH:1]1([C:7]([NH2:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7413Cyclohexanecarboxylic acidHCID 14923Ammonium HydroxideHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 14283CyclohexanecarboxamideYield 112%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of cyclohexanecarboxylic acid (1.00 g, 7.80 mmol) in EtOAc (10 mL) was treated with CDI (1.581 g, 9.75 mmol), stirred at RT for 20 minutes, treated with ammonium hydroxide (5.00 mL, 70.0 mmol) and stirred for 20 minutes. The mixture was treated with satd. NaHCO3, extracted with EtOAc (2×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford cyclohexanecarboxamide (1.109 g, 112%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 5.61 (s, 2H), 2.13 (m, 1H), 1.89 (m, 2H), 1.78 (m, 2H), 1.66 (m, 1H), 1.42 (m, 2H), 1.24 (m, 3H).

Workup

  1. stirringstirred for 20 minutes
  2. additionThe mixture was treated with satd
  3. extractionNaHCO3, extracted with EtOAc (2×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2b3572eec7d44fe7aed723157f41bdae
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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