Dimethylamine → HCID 54295159, compound

HRID 1196077Notes

Reaction equation

HRID 1196077 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH2:8])=[O:7].[CH3:9][NH:10][CH3:11]>C(O)C>[CH3:9][N:10]([CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH2:8])=[O:7]

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 15101532HCID 15101532, compound

Product 1

HCID 54295159HCID 54295159, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5-Bromopentanamide (10.11 g) was dissolved in ethanol (50 ml) and a 33% solution of dimethylamine in ethanol (20 ml) added. The solution was allowed to stand at room temperature for 3 hours, more dimethyl amine added (20 ml) and the solution allowed to stand at room temperature for 18 hours. The solution was evaporated to an oil which was dissolved in dilute HCl and the solution of pH 2 was washed twice with dichloromethane, basified with NaOH, saturated with NaCl and extracted 10 times with dichloromethane. The combined latter extracts were dried over K2CO3 and evaporated to give 5-dimethylaminopentanamide as acolourless solid (5.72 g, 70%) (mp 86°-7°).

Workup

  1. waitto stand at room temperature for 18 hours
  2. customThe solution was evaporated to an oil which
  3. dissolutionwas dissolved in dilute HCl
  4. washthe solution of pH 2 was washed twice with dichloromethane
  5. extractionextracted 10 times with dichloromethane
  6. dry with materialThe combined latter extracts were dried over K2CO3
  7. customevaporated

Sources & evidence

ORD record
ord-09d25753c7bc4f6c99db7c4c5b95c457
Source dataset
uspto-grants-1992_05
Patent number
US05112922

Reaction notes

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