Acetic Acid → HCID 22139317, compound

HRID 1825753Notes

Reaction equation

HRID 1825753 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C=O.[C:9](O)(=O)C.[NH:13]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:22]=[O:23])[C:16]=2[CH:15]=[CH:14]1>O>[O:4]1[CH2:5][CH2:6][N:1]([CH2:9][C:15]2[C:16]3[C:17]([CH:22]=[O:23])=[CH:18][CH:19]=[CH:20][C:21]=3[NH:13][CH:14]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8083MorpholineHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 22139317HCID 22139317, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Morpholine (0.24 ml, 2.7 mmol) and formaldehyde (37% aq; 0.21 ml, 2.7 mmol) were added to glacial acetic acid (3 ml) at 0° C. After stirring for 15 minutes 4-indolcarboxaldehyde (0.27 g, 1.9 mmol) was added. The mixture was stirred 5 minutes at 0° C. and then 3½h at room temperature, prior to the addition of water (6 ml) and washing with ether. The aqueous layer was made alkaline with 2N NaOH and then extracted with dichloromethane. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and evaporated to afford 0.46 g of the entitled product as an oil which was used without further purification.

Workup

  1. additionwas added
  2. washwashing with ether
  3. extractionextracted with dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-16eb1a25a4974f5f99a9805fc8fd024c
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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