3-(Dimethylamino)-1,2-propanediol → Dodma

HRID 330577

Reaction equation

HRID 330577 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH:4]([OH:7])[CH2:5][OH:6].C[C:10]([CH3:13])([O-])[CH3:11].[K+].C1(C)C(S(O[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])(=O)=O)=CC=CC=1>>[CH2:42]([O:7][CH:4]([CH2:5][O:6][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]/[CH:31]=[CH:30]\[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:11][CH2:10][CH3:13])[CH2:3][N:2]([CH3:8])[CH3:1])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]/[CH:34]=[CH:33]\[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25]

Participants

4

Reactant 3

HCID 790783-(Dimethylamino)-1,2-propanediolHCID 23665647Potassium tert-butoxideHCID 86743716Oleyl toluenesulfonate

Product 1

HCID 11181107DodmaYield 72.6%

Procedure

In accordance with Reaction Scheme I, a mixture of 3-(dimethylamino)-1,2-propanediol (1.19 g, 10 mmol), potassium tert-butoxide (3.36 g, 30 mmol) and oleyl toluenesulfonate (12.7 g, 30 mmol) in xylenes (50 ml) was stirred at room temperature under house vacuum (approx. 30 torr) for 0.5 hour. The mixture was heated to 50° C. and stirred for an additional 0.25 hour. The vacuum was removed and the reaction vessel was filled with nitrogen gas to room pressure (approx. 1 atm.). The temperature was increased until the reaction boiled (approximately 140° C.) and the mixture was stirred at reflux for 3 hours. The mixture was diluted with hexane (100 ml) and extracted with water (2×50 ml). The organic layer was concentrated, applied to a column of silica gel (150 g) packed in hexanes in ether (1:2), then eluted with the same solvent mixture to give the title compound (4.5 g) as an oil.

Workup

  1. customIn accordance with Reaction Scheme I
  2. temperatureThe mixture was heated to 50° C.
  3. stirringstirred for an additional 0.25 hour
  4. customThe vacuum was removed
  5. additionthe reaction vessel was filled with nitrogen gas to room pressure (approx. 1 atm.)
  6. temperatureThe temperature was increased until the reaction
  7. custom(approximately 140° C.)
  8. stirringthe mixture was stirred
  9. temperatureat reflux for 3 hours
  10. additionThe mixture was diluted with hexane (100 ml)
  11. extractionextracted with water (2×50 ml)
  12. concentrationThe organic layer was concentrated
  13. washeluted with the same solvent mixture

Sources & evidence

ORD record
ord-0209caa588a445c9a57212904eca4523
Source dataset
uspto-grants-1990_01
Patent number
US04897355

Linked notes

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