Bis(2-Methoxyethyl)amine → HCID 21464486, compound

HRID 1939847Notes

Reaction equation

HRID 1939847 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][CH3:9].[C:10]1(=[O:17])[O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][O:8][CH3:9])[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][OH:17]

Participants

4

Reactant 2

HCID 2383Bis(2-Methoxyethyl)amineHCID 10401epsilon-CAPROLACTONE2×

Product 1

HCID 21464486HCID 21464486, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of Bis(2-methoxyethyl)amine (11.85 g) and toluene (100 mL) was warmed to 65° C. under nitrogen. A solution of epsilon-Caprolactone (9.23 g) in toluene (35 mL) was added over several minutes. The mixture was stirred at this temperature until all the caprolactone was consumed, as determined by thin layer chromatography (silica gel plate), 4:1 ethanol/NH4OH). After 20 hours, an additional portion of bis(2-methoxyethyl)amine (3.1 g) was added and heating continued. After about 36 hours, all caprolactone had been consumed. The solvent was removed in vacuo on a rotary evaporator to afford the product as an oil (21.7 g).

Workup

  1. customwas consumed
  2. additionan additional portion of bis(2-methoxyethyl)amine (3.1 g) was added
  3. temperatureheating
  4. waitAfter about 36 hours
  5. customall caprolactone had been consumed
  6. customThe solvent was removed in vacuo on a rotary evaporator

Sources & evidence

ORD record
ord-7c62bc31c806431fb1cfbf639d81ca24
Source dataset
uspto-grants-1997_12
Patent number
US05698016

Reaction notes

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