Dimethylamine → HCID 53947707, compound

HRID 1196079Notes

Reaction equation

HRID 1196079 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:7].[CH3:17][NH:18][CH3:19]>C(O)C.Cl>[CH3:17][N:18]([CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:7]

Participants

5

Reactant 2

HCID 674Dimethylamine2×HCID 54265335HCID 54265335, compound

Product 1

HCID 53947707HCID 53947707, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

5-Bromo-N-octylpentanamide (17.25 g) was dissolved in ethanol (50 ml) and a 33% solution of dimethylamine in ethanol (20 ml) was added. The solution was allowed to stand at room temperature for 3 hours, more dimethylamine (10 ml) added and the solution allowed to stand at room temperature for 18 hours. The solution was evaporated to give an oil, which was dissolved in dilute HCl and the solution at pH 5.5 was washed with dichloromethane. The pH was then raised to 7.5 and extracted twice with dichloromethane at this pH. The combined latter organic extracts were dried over MgSO4 and evaporated to give 5-dimethylamino-N-octylpentanamide as an oil (10.6 g, 70%).

Workup

  1. waitto stand at room temperature for 18 hours
  2. customThe solution was evaporated
  3. customto give an oil, which
  4. washthe solution at pH 5.5 was washed with dichloromethane
  5. temperatureThe pH was then raised to 7.5
  6. extractionextracted twice with dichloromethane at this pH
  7. dry with materialThe combined latter organic extracts were dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-ca5a42d7f4484f46a3b798c971ced9e8
Source dataset
uspto-grants-1992_05
Patent number
US05112922

Reaction notes

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