Pyridine → HCID 90034468, compound

HRID 1481265Notes

Reaction equation

HRID 1481265 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8](Cl)=[O:9])[CH2:3]1.Cl.[CH3:12][NH:13][O:14][CH3:15].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:15][O:14][N:13]([CH3:12])[C:8]([CH:4]1[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3]1)=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 18718207HCID 18718207, compound

Product 1

HCID 90034468HCID 90034468, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-methylcyclohexanecarbonyl chloride (1.13 g, 7.03 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.755 g, 7.74 mmol) in CHCl3 (70 mL) at 0° C. was added pyridine (1.252 mL, 15.48 mmol) dropwise. The ice bath was removed and the mixture was warmed to RT. After 1 h, the reaction was evaporated to dryness, diluted with 1:1 mixture of ether and CH2Cl2 (40 ml) and then washed with brine. The aqueous layer was washed once more with 1:1 mixture of ether and CH2Cl2. The organic layers were combined, dried with MgSO4, filtered, and concentrated to afford the crude N-methoxy-N,3-dimethylcyclohexanecarboxamide (1.1 g, 84% yield) as clear yellowish oil which was used without further purification. MS (ESI) m/z: 186.1 (M+H)+. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.74-3.65 (m, 3H), 3.20-3.14 (m, 3H), 2.71 (m., 1H), 1.85-1.12 (m, 10H), 0.94-0.88 (m, 3H)

Workup

  1. customThe ice bath was removed
  2. customthe reaction was evaporated to dryness
  3. additiondiluted with 1:1 mixture of ether and CH2Cl2 (40 ml)
  4. washwashed with brine
  5. washThe aqueous layer was washed once more with 1:1 mixture of ether and CH2Cl2
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-504a6b339d9e4b6e815c64f04d883bcf
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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