Triethanolamine → HCID 21872526, compound

HRID 650461Notes

Reaction equation

HRID 650461 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][CH2:20][O:21][CH2:22]Cl.[CH3:24][O:25][CH2:26][CH2:27][O:28][CH2:29]OCCl.[O:33]1[CH2:37]C[CH2:35][CH2:34]1>CO>[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22][O:10][CH2:9][CH2:8][N:7]([CH2:14][CH2:15][O:16][CH2:29][O:28][CH2:27][CH2:26][O:25][CH3:24])[CH2:11][CH2:12][O:13][CH2:2][O:4][CH2:35][CH2:34][O:33][CH3:37]

Participants

7

Reactant 5

HCID 7618TriethanolamineHCID 8028Tetrahydrofuran2×HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 131286991-[(Chloromethoxy)methoxy]-2-methoxyethaneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 21872526HCID 21872526, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 135.3 grams of potassium t-butoxide in 900 ml of tetrahydrofuran, 50.0 grams of triethanolamine in 100 ml of tetrahydrofuran was added dropwise over 10 minutes while stirring under ice cooling. After 40 minutes of stirring, 150.4 grams of chloromethyl 2-methoxyethyl ether was added dropwise over 30 minutes while continuing stirring under ice cooling. After 30 minutes of stirring, 37.6 grams of potassium t-butoxide was added while continuing stirring under ice cooling. After 20 minutes of stirring, 41.8 grams of chloromethyl (2-methoxyethoxy)methyl ether was added dropwise over 10 minutes while continuing stirring under ice cooling. After 40 minutes of stirring, 250 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 dissolved in 2,000 ml of methylene chloride. Using a separatory flask, the solution was washed three times with 200 ml of water. The organic phase was concentrated in vacuum. On analysis by 1H-NMR, the resulting oily matter was found to be tris[2-(2-methoxyethoxy)-methoxyethyl]amine, designated Amine 2. Amount 103.9 grams, yield 70.0%.

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. dissolutionthe resulting oily matter was dissolved in 2,000 ml of methylene chloride
  14. washthe solution was washed three times with 200 ml of water
  15. concentrationThe organic phase was concentrated in vacuum

Sources & evidence

ORD record
ord-4fe3e45a710740a4aa88b1126655e625
Source dataset
uspto-grants-2001_08
Patent number
US06274286B1

Reaction notes

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