Dibutylamine → N,N-dibutylpentanamide

HRID 1395865Notes

Reaction equation

HRID 1395865 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[C:10](Cl)(=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14]>C(OCC)C>[CH2:1]([N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8148Dibutylamine2×HCID 61186Valeryl chloride

Product 1

HCID 304103N,N-dibutylpentanamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

a round-bottom flask containing a magnetic stirring bar, diethyl ether (400 mL) and N,N-dibutylamine (37 mL, 0.22 mol, 2.2 equiv.) was cooled in ice for 30 minutes. Valeroyl chloride (12.0 mL, 0.099 mol, 1.0 equiv.) was combined with diethyl ether (75 mL) and added dropwise over 30 minutes to the stirring dibutylamine solution on ice. A white precipitate, likely the amine's chloride salt, was observed. The flask was removed from ice and stirred at room temperature for 3 h. Two 500 mL extractions were performed with dilute HCl (10 mL conc. HCl per 500 mL extraction) to remove the excess amine and ammonium chloride byproduct. The diethyl ether layer was retained and dried with MgSO4. Diethyl ether was removed under rotary evaporation and high vacuum, leaving crude N,N-dibutylpentanamide.

Workup

  1. additiona round-bottom flask containing a magnetic stirring bar
  2. customThe flask was removed from ice
  3. extractionTwo 500 mL extractions
  4. customto remove the excess amine and ammonium chloride byproduct
  5. dry with materialdried with MgSO4
  6. customDiethyl ether was removed under rotary evaporation and high vacuum

Sources & evidence

ORD record
ord-29c0bded4c804bdab46d5171c1f63922
Source dataset
uspto-grants-2014_12
Patent number
US08900444B2

Reaction notes

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