Dimethylamine → HCID 54149543, compound

HRID 1196076Notes

Reaction equation

HRID 1196076 reaction equation
Br[CH2:2][CH2:3][C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:5].[CH3:15][NH:16][CH3:17]>C(O)C.Cl>[CH3:15][N:16]([CH3:17])[CH2:2][CH2:3][C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:5]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 53648437HCID 53648437, compound

Product 1

HCID 54149543HCID 54149543, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

3-Bromo-N-octylpropanamide (21.3 g) was dissolved in ethanol (50 ml) and a 33% solution of dimethylamine in IMS (100 ml) was added. The solution was allowed to stand at 20° for 72 hours then evaporated to give a yellow oil. This oil was dissolved in dilute HCl to give a solution of pH 4 which was washed twice with dichloromethane, basified with dilute aqueous sodium hydroxide solution and extracted with dichloromethane three times. The latter dichloromethane extracts were dried and evaporated to a pale yellow oil. Distillation of the residue gave 3-dimethylamino-N-octylpropanamide as a colourless oil (15.1 g, 83% yield) (bp 135°-8°/0.15mm).

Workup

  1. customthen evaporated
  2. customto give a yellow oil
  3. customto give a solution of pH 4 which
  4. washwas washed twice with dichloromethane
  5. extractionextracted with dichloromethane three times
  6. dry with materialThe latter dichloromethane extracts were dried
  7. customevaporated to a pale yellow oil
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-2095f3e60e394e56a2d3413d188bd603
Source dataset
uspto-grants-1992_05
Patent number
US05112922

Reaction notes

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