Triethylamine → HCID 86745864, compound

HRID 1197161Notes

Reaction equation

HRID 1197161 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([N:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:8])[CH2:5][OH:6].[CH2:27](N(CC)CC)C.Cl[P:35]1(=[O:40])[O:39]CC[O:36]1>C1C=CC=CC=1>[P:35]([O:6][CH2:5][CH2:4][N+:7]([CH3:9])([CH3:27])[CH3:8])([OH:40])([OH:39])=[O:36].[CH3:1][O:2][CH2:3][CH:4]([N:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:8])[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 810872-Chloro-1,3,2-dioxaphospholane 2-oxideHCID 198978403-methoxy-2-(N-methyl-octadecylamino)propanol

Product 1

HCID 86745864HCID 86745864, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
5 °C

Procedure

Compound of the formula Ia wherein R1 =CH3, R2 =C18H37, R3 =CH3, ##STR12## 2 g (5 mmol) of 3-methoxy-2-(N-methyl-octadecylamino)propanol (IIa) and 3 ml of triethylamine were dissolved in 20 ml of dry benzene, and the mixture was cooled to 5° C. under nitrogen circulation. 1 g (7 mmol) of 2-chloro-2-oxo-1,3,2-dioxaphospholane in 4 ml of benzene was added under stirring, and stirring was continued overnight. The amino salt was filtered off and washed with benzene. The filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in 20 ml of dry methyl cyanide and transferred to a reactor. 20 ml of methyl cyanide, saturated with gaseous trimethylamine, was added, and the mixture was heated at 65° C. for 24 hours. A solid separated on cooling. It was filtered off and chromatographed on silica gel (eluent chloroform:methanol 90:10, then 70:30 by volume, then methanol) to yield 1.1 g (39%) of the title compound.

Workup

  1. stirringstirring
  2. filtrationThe amino salt was filtered off
  3. washwashed with benzene
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in 20 ml of dry methyl cyanide
  6. customtransferred to a reactor
  7. addition20 ml of methyl cyanide, saturated with gaseous trimethylamine, was added
  8. temperaturethe mixture was heated at 65° C. for 24 hours
  9. customA solid separated
  10. temperatureon cooling
  11. filtrationIt was filtered off
  12. customchromatographed on silica gel (eluent chloroform:methanol 90:10

Sources & evidence

ORD record
ord-a498470fd4a24a8689218fa5a7b6b689
Source dataset
uspto-grants-1992_05
Patent number
US05116992

Reaction notes

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