2-Methoxyethylamine → HCID 13645523, compound

HRID 476587Notes

Reaction equation

HRID 476587 reaction equation
F[C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:9]=2[CH3:25])=[O:7])=[CH:4][CH:3]=1.[CH3:28][O:29][CH2:30][CH2:31][NH2:32].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:25][C:9]1[N:10]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:11]2[C:16]([C:8]=1[C:6](=[O:7])[C:5]1[CH:26]=[CH:27][C:2]([NH:32][CH2:31][CH2:30][O:29][CH3:28])=[CH:3][CH:4]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 10384274HCID 10384274, compound

Product 1

HCID 13645523HCID 13645523, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 10 g. (0.027 mole) of 3-(4-fluorobenzoyl)-2-methyl-1-[2-(4-morpholinyl)ethyl]-1H-indole, (Example 1Q) 2.5 g. (0.033 mole) of 2-methoxyethylamine and 7.6 g. (0.054 mole) of potassium carbonate in 15 ml of DMSO was heated at 95° C. under nitrogen and the mixture then poured into ice water. The solid which separated was collected, dissolved in methylene dichloride and the solution washed with brine, dried over magnesium sulfate, filtered and taken to dryness in vacuo. Recrystallization of the residue from ethyl acetate-ether afforded 4.2 g (37%) of 2-methyl-3-[4-(2-methoxyethylamino)benzoyl]-1-[2-(4-morpholinyl)ethyl]-1H-indole, m.p. 121°-123° C.

Workup

  1. additionA mixture of 10 g
  2. customThe solid which separated
  3. customwas collected
  4. dissolutiondissolved in methylene dichloride
  5. washthe solution washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customRecrystallization of the residue from ethyl acetate-ether

Sources & evidence

ORD record
ord-61213e2cb0f14b1e939131fee045b0a6
Source dataset
uspto-grants-1989_12
Patent number
US04885295

Reaction notes

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