Water → HCID 14178413, compound

HRID 2235226Notes

Reaction equation

HRID 2235226 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:9].O>C(#N)C>[CH:11]1([N:10]2[CH2:4][CH2:5][CH2:6][CH2:7][C:8]2=[O:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydride2×HCID 116729745-Chloro-N-cyclohexylpentanamide

Product 1

HCID 14178413HCID 14178413, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add NaH (550 g, 14 mmol) into a solution of 5-chloro-N-cyclohexylpentanamide (3 g, 14 mmol) in acetonitrile (100 mL). Stir the reaction at room temperature for 12 hours. Add NaH (1 g, 28 mmol) and continue to stir for 2 days. Pour the reaction into ice and water. Wash the reaction with brine, dry with sodium sulfate, filter and concentrate. Purify the residue by column chromatography to afford the title compound (1.5 g, 60%) as a white solid. 1H NMR (CDCl3): 4.44-4.54 (m, 1H), 3.14 (m, 2H), 2.36-2.42 (m, 2H), 1.70-1.84 (m, 6H), 1.60-1.70 (m, 4H), 1.32-1.48 (m, 4H), 1.00-1.12 (m, 1H).

Workup

  1. customthe reaction at room temperature for 12 hours
  2. stirringto stir for 2 days
  3. additionPour
  4. washWash
  5. customthe reaction with brine
  6. dry with materialdry with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the residue by column chromatography

Sources & evidence

ORD record
ord-dc386bf63edf4f6886ae1aa8b1f8f32f
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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