Ammonium Hydroxide → HCID 178461259, compound

HRID 1049321Notes

Reaction equation

HRID 1049321 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.C1N=C[N:13](C(N2C=NC=C2)=O)C=1.[OH-].[NH4+]>CCOC(C)=O>[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([NH2:13])=[O:10])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 178461286HCID 178461286, compound

Product 1

HCID 178461259HCID 178461259, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of trans-4-methylcyclohexane carboxylic acid (1.00 g, 7.03 mmol) in EtOAc (15 mL) was treated with CDI (1.425 g, 8.79 mmol) and stirred at RT for 20 minutes. Ammonium hydroxide (˜14M, 5.00 mL, ˜70.0 mmol) was added, the mixture stirred for 20 minutes, then concentrated to dryness. The material was treated with satd. NaHCO3 and the solids collected via filtration and dried to afford trans-4-methylcyclohexanecarboxamide (842 mg, 85%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.13 (s, 1H), 6.61 (s, 1H), 1.94 (m, 1H), 1.70 (m, 4H), 1.25 (m, 3H), 0.84 (m, 5H); MS (ESI) m/z: 142.1 (M+H+).

Workup

  1. stirringthe mixture stirred for 20 minutes
  2. concentrationconcentrated to dryness
  3. additionThe material was treated with satd
  4. filtrationNaHCO3 and the solids collected via filtration
  5. customdried

Sources & evidence

ORD record
ord-a74a96e08061457589fb4c63ec89075d
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

Loading…