Potassium Hydroxide → Dodma

HRID 1741812Notes

Reaction equation

HRID 1741812 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH:4]([OH:7])[CH2:5][OH:6].[OH-].[K+].S(O[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=O)(=O)C>C1(C)C(C)=CC=CC=1>[CH2:16]([O:7][CH:4]([CH2:5][O:6][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:3][N:2]([CH3:8])[CH3:1])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 790783-(Dimethylamino)-1,2-propanediolHCID 6016198Oleyl methane sulfonate

Product 1

HCID 11181107DodmaYield 76%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

To a three-necked, 2-liter round bottom flask equipped with a Dean-Stork trap were added 3 -dimethylamino-1,2 -propanediol (6.08 g, 51.1 mmoles), xylene (1300 ml) and KOH (8.0 g). The solution was refluxed for 2 hours while removing water azeotropically via the Dean-Stork trap. Oleyl mesylate (40.0 g, 115.6 mmoles) in 100 ml xylene was added to the reaction mixture drop-wise in 30 minutes. Refluxing was continued for 3 hours and the reaction mixture concentrated to a gum. The gum was triturated with 400 ml hexane and filtered. The solid was washed with 100 ml hexane followed with 200 ml ethyl acetate. The filtrates were combined, concentrated and subjected to f lash chromatography. 2,3-dioleyloxy-1- (N, N-dimethylamino) propane was obtained as a colorless oil in 76% yield, TLC: Rf =0.37 (Silica gel: 5% EtOAc: hexane); IR: 2925, 2850, 1469, 1120, 1040 cm-1 ; HNMR (CDCl3) δ 5.35 (t, 4H) , 4.13 (q, 1H) 3.4-3.65 (m, 6H), 2.35-2.45 (m, 2H) , 2.25 (S, 6H) , 1.95-2.05 (m, 8H) , 1.5-1.65 (m, 4H) , 1.2-1.45 (m, 4H) 0.9 (t, 6H).

Workup

  1. customTo a three-necked, 2-liter round bottom flask equipped with a Dean-Stork trap
  2. temperatureThe solution was refluxed for 2 hours
  3. customwhile removing water azeotropically via the Dean-Stork trap
  4. temperatureRefluxing
  5. concentrationthe reaction mixture concentrated to a gum
  6. customThe gum was triturated with 400 ml hexane
  7. filtrationfiltered
  8. washThe solid was washed with 100 ml hexane
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2f15ec61c7314f8d814d38f22a35de52
Source dataset
uspto-grants-1994_08
Patent number
US05334761

Reaction notes

Loading…