Methanol → 2-(Methoxymethoxy)-N,N-bis[2-(methoxymethoxy)ethyl]ethan-1-amine

HRID 650460Notes

Reaction equation

HRID 650460 reaction equation
C[C:2](C)([O-:4])C.[K+].[N:7]([CH2:14][CH2:15][OH:16])([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][OH:10].[CH3:17][O:18][CH2:19]Cl.[CH3:21]O.[O:23]1[CH2:27]CC[CH2:24]1>>[CH3:17][O:18][CH2:19][O:10][CH2:9][CH2:8][N:7]([CH2:14][CH2:15][O:16][CH2:21][O:4][CH3:2])[CH2:11][CH2:12][O:13][CH2:24][O:23][CH3:27]

Participants

6

Reactant 5

HCID 887MethanolHCID 7618TriethanolamineHCID 7864Chloromethyl Methyl Ether2×HCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxide2×

Product 1

HCID 218723762-(Methoxymethoxy)-N,N-bis[2-(methoxymethoxy)ethyl]ethan-1-amineYield 74.2%

Procedure

To a suspension of 270.6 grams of potassium t-butoxide in 1,800 ml of tetrahydrofuran, 100.0 grams of triethanolamine in 200 ml of tetrahydrofuran was added dropwise over 10 minutes while stirring under ice cooling. After 40 minutes of stirring, 194.5 grams of chloromethyl methyl ether was added dropwise over 30 minutes while continuing stirring under ice cooling. After 30 minutes of stirring, 75.2 grams of potassium t-butoxide was added while continuing stirring under ice cooling. After 20 minutes of stirring, 54.0 grams of chloromethyl methyl ether was added dropwise over 10 minutes while continuing stirring under ice cooling. After 40 minutes of stirring, 500 ml of methanol was added. After 30 minutes of stirring, the reaction solution was filtered with a sufficient amount of Celite, and the residue was washed with ether. The filtrate was concentrated under vacuum, and the resulting oily matter was distilled under vacuum. On analysis by 1H-NMR, the thus collected oily matter was found to be tris(2-methoxymethoxyethyl)amine, designated Amine 1. Amount 139.9 grams, yield 74.2%.

Workup

  1. additionwas added dropwise over 10 minutes
  2. stirringAfter 40 minutes of stirring
  3. stirringwhile continuing stirring under ice cooling
  4. stirringAfter 30 minutes of stirring
  5. stirringwhile continuing stirring under ice cooling
  6. stirringAfter 20 minutes of stirring
  7. stirringwhile continuing stirring under ice cooling
  8. stirringAfter 40 minutes of stirring
  9. stirringAfter 30 minutes of stirring
  10. filtrationthe reaction solution was filtered with a sufficient amount of Celite
  11. washthe residue was washed with ether
  12. concentrationThe filtrate was concentrated under vacuum
  13. distillationthe resulting oily matter was distilled under vacuum

Sources & evidence

ORD record
ord-064f18fcda9c43948a72dcd3d568937e
Source dataset
uspto-grants-2001_08
Patent number
US06274286B1

Reaction notes

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