Ethylene Glycol → 6-fluoro-3-(piperidin-4-yl)-1H-indole

HRID 1248222Notes

Reaction equation

HRID 1248222 reaction equation
C([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[C:23]3[C:18](=[CH:19][C:20]([F:24])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+].C(O)CO>O>[F:24][C:20]1[CH:19]=[C:18]2[C:23]([C:15]([CH:12]3[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]3)=[CH:16][NH:17]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 13476528HCID 13476528, compound

Product 1

HCID 110960776-fluoro-3-(piperidin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 24 parts of 1-benzoyl-4-(6-fluoro-1H-indol-3-yl)-piperidine, 70 parts of potassium hydroxide, 495 parts of 1,2-ethanediol and 80 parts of water is stirred and refluxed for 6 hours. The reaction mixture is cooled and 500 parts of water are added while stirring. The precipitated product is filtered off, washed with water and petroleumether and dried in vacuo at 80° C., yielding 16 parts of 6-fluoro-3-(4-piperidinyl)-1H-indole; mp. 224° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureThe reaction mixture is cooled
  3. stirringwhile stirring
  4. filtrationThe precipitated product is filtered off
  5. washwashed with water and petroleumether
  6. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-506ffe53470c4853b1950150ce4ba417
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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