Dimethylamine → N,N-Dimethylheptanamide

HRID 1031405Notes

Reaction equation

HRID 1031405 reaction equation
C(OC(Cl)=O)C.[C:7]([OH:15])(=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:16]([N:18](CC)[CH2:19]C)C.CNC>O1CCCC1.C(O)C>[CH3:16][N:18]([CH3:19])[C:7](=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8094Heptanoic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 14221N,N-Dimethylheptanamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethylchloroformate (18.3 ml) was added slowly to a solution of heptanoic acid (20.0 g) and triethylamine (26.7 ml) in tetrahydrofuran (250 ml), maintained at -10°. The resulting mixture was stirred at 10° for 0.75 hour, cooled to 5° and a 33% solution of dimethylamine in ethanol (41.6 ml) added dropwise. This mixture was then allowed to warm to room temperature and stirred for 4 hours. The mixture was filtered and the filtrate evaporated to dryness. The residue was dissolved in chloroform (250 ml) and washed with 1% aqueous sodium carbonate solution (200 ml) and water, then dried and evaporated. The residual oil was chromatographed on silica gel to give N,N-dimethylheptanamide (14.1 g) as a colourless oil.

Workup

  1. temperaturemaintained at -10°
  2. temperaturecooled to 5°
  3. stirringstirred for 4 hours
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated to dryness
  6. dissolutionThe residue was dissolved in chloroform (250 ml)
  7. washwashed with 1% aqueous sodium carbonate solution (200 ml) and water
  8. customdried
  9. customevaporated
  10. customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-71e2aa79daed492389ddb4bbb1e4438c
Source dataset
uspto-grants-1990_09
Patent number
US04954339

Reaction notes

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