N,N-Dimethyl-1,3-propanediamine → Tetradecanamide, N-[3-(dimethylamino)propyl]-

HRID 275236Notes

Reaction equation

HRID 275236 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].[C:8](Cl)(=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 66986Myristoyl chloride

Product 1

HCID 170759Tetradecanamide, N-[3-(dimethylamino)propyl]-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.0 g. (0.0196 moles) of 3-dimethylaminopropylamine in 40 ml chloroform was added dropwise to an ice cold chloroform solution (50 ml) of myristoyl chloride (4.17 g., 0.0169 moles). After addition, the ice bath was removed and the solution was stirred for 2 hours. A 25 ml aqueous sodium bicarbonate solution was added and stirred for 30 minutes. The organic layer was then washed with 30 ml aqueous sodium bicarbonate/sodium chloride solution and dried with magnesium sulfate. The solution was concentrated in vacuo and the amide was recrystallized in ethyl acetate to yield 3.29 g. (0.0105 moles, 62.3%) of the subject compound.

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. additionA 25 ml aqueous sodium bicarbonate solution was added
  4. stirringstirred for 30 minutes
  5. washThe organic layer was then washed with 30 ml aqueous sodium bicarbonate/sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe solution was concentrated in vacuo
  8. customthe amide was recrystallized in ethyl acetate
  9. customto yield 3.29 g

Sources & evidence

ORD record
ord-f3e0221111b143b4bf96a6ebd653cbc0
Source dataset
uspto-grants-1995_02
Patent number
US05393491

Reaction notes

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