Water → 1,1'-(9H-Fluorene-2,7-diyl)bis(4-(1-piperidinyl)-1-butanone)

HRID 461956Notes

Reaction equation

HRID 461956 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Cl)=[CH:14][CH:15]=3)[CH2:10][C:9]=2[CH:8]=1)=[O:6].[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[I-].[K+].O>CC(=O)CC>[N:26]1([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:19]=[CH:18][C:17]3[C:16]4[C:11](=[CH:12][C:13]([C:20](=[O:25])[CH2:21][CH2:22][CH2:23][N:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)=[CH:14][CH:15]=4)[CH2:10][C:9]=3[CH:8]=2)=[O:6])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 8082PiperidineHCID 131705491,1'-(9H-Fluorene-2,7-diyl)bis(4-chlorobutan-1-one)

Product 1

HCID 1602411,1'-(9H-Fluorene-2,7-diyl)bis(4-(1-piperidinyl)-1-butanone)

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 18.8g (0.05 mole) of 2,7-bis(4-chlorobutyryl)fluorene, prepared in Example 1, 34.0g (0.4 mole) of piperidine, 16.6g (0.1 mole) of potassium iodide in 200 ml of butanone was stirred and refluxed for three days. The reaction mixture was poured into 1000 ml of water, and the solid which precipitated was filtered and recrystallized twice from chloroformacetone to give the desired product. M.P. 157°-159° C, λmax0.1NHCl 325, Elcm1% 816.

Workup

  1. temperaturerefluxed for three days
  2. customthe solid which precipitated
  3. filtrationwas filtered
  4. customrecrystallized twice from chloroformacetone

Sources & evidence

ORD record
ord-2db8b474bed34cc889765a472efe6b57
Source dataset
uspto-grants-1977_12
Patent number
US04064347

Reaction notes

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