Ethanol → HCID 53702167, compound

HRID 476586Notes

Reaction equation

HRID 476586 reaction equation
C[C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH:4]=[CH:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:9]=1[CH3:25])=[O:7].[F:30]C1C=CC=CC=1C=O.C(O)C.[OH-].[K+]>C(OCC)(=O)C>[F:30][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH:4]=[CH:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[C:9]=1[CH3:25])=[O:7]

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 67970o-FluorobenzaldehydeHCID 53923408HCID 53923408, compound

Product 1

HCID 53702167HCID 53702167, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following a procedure similar to that described in Example 20A above, 14.75 g. (0.0516 mole) of 3-acetyl-2-methyl-1-[2-(4-morpholinyl)ethyl]-1H-indole (Example 20A) was reacted with 2-fluorobenzaldehyde in 260 ml. of ethanol in the presence of 3.44 g. (0.061 mole) of potassium hydroxide pellets and the product, in the form of the free base, recrystallized from ethyl acetate to give 10.0 g (54%) of 3-(2-fluorocinnamoyl)-2-methyl-1-[2-(4-morpholinyl)ethyl]-1H-indole, m.p. 113°-116° C.

Sources & evidence

ORD record
ord-4f90ef48f5204388b4dea4355249eba3
Source dataset
uspto-grants-1989_12
Patent number
US04885295

Reaction notes

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