Dimethylamine → HCID 54318035, compound

HRID 485316Notes

Reaction equation

HRID 485316 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2.[OH-].[K+]>O1CCOCC1.C(O)(=O)C>[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:8]=1[C:18]1[NH:19][C:20]2[C:25]([C:26]=1[CH2:3][N:4]([CH3:1])[CH3:5])=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

7

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 128548642-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)-1H-indole

Product 1

HCID 54318035HCID 54318035, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 20.6 ml. (0.24 mole) 37% aqueous formaldehyde, 18 ml. (0.12 mole) 40% aqueous dimethylamine and 80 ml. acetic acid is cooled to 0° and treated by dropwise addition with 25.5 g. (0.113 mole) 2-(5-methyl-3-phenyl-4-isoxazolyl)-indole in a solution of 45 ml. acetic acid and 125 ml. dioxane. After addition is complete the mixture is stirred for 1 hour at room temperature and poured onto 500 ml. ice-water. The resulting solution is made basic with 20% potassium hydroxide and then extracted with methylene chloride. The methylene chloride is washed with water, brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 2-(5-methyl-3-phenyl-4-isoxazolyl)-3-(dimethylaminomethyl)-indole.

Workup

  1. additionA mixture of 20.6 ml
  2. additiontreated by dropwise addition with 25.5 g
  3. additionAfter addition
  4. additionpoured onto 500 ml
  5. extractionextracted with methylene chloride
  6. washThe methylene chloride is washed with water, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-7eb9868160554928a356a2f2c0825cf3
Source dataset
uspto-grants-1985_08
Patent number
US04536499

Reaction notes

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