Dimethylamine → HCID 12854868, compound

HRID 1262716Notes

Reaction equation

HRID 1262716 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[CH2:6]([C:8]1[C:12]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([CH3:22])[O:10][N:9]=1)[CH3:7].[OH-].[K+]>O1CCOCC1.C(O)(=O)C>[CH2:6]([C:8]1[C:12]([C:13]2[NH:14][C:15]3[C:20]([C:21]=2[CH2:3][N:4]([CH3:1])[CH3:5])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([CH3:22])[O:10][N:9]=1)[CH3:7]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 130386862-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indole

Product 1

HCID 12854868HCID 12854868, 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 the dropwise addition of 25.5 g. (0.113 mole) 2-(3-ethyl-5-methyl-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 a gum that crystallizes to give 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-(dimethylaminomethyl)-indole; m.p. 88° to 90° C.

Workup

  1. additionA mixture of 20.6 ml
  2. additiontreated by the dropwise addition of 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
  10. customto give a gum that
  11. customcrystallizes

Sources & evidence

ORD record
ord-98ae9276883945a2be6aedd39da59269
Source dataset
uspto-grants-1984_06
Patent number
US04453001

Reaction notes

Loading…