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

HRID 1576962Notes

Reaction equation

HRID 1576962 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 18.8 g (0.05 mole) of 2,7-bis(4-chlorobutyryl)fluorene, 34.0 g (0.4 mole) of piperidine, and 16.6 g (0.1 mole) of potassium iodide in 200 ml of butanone is stirred and refluxed for 3 days. The reaction mixture is poured into 1000 ml of water, and the solid which precipitates is filtered and recrystallized twice from chloroform-acetone to give the desired 2,7-bis(4-piperidinobutyryl)fluorene as the free base.

Workup

  1. temperaturerefluxed for 3 days
  2. customthe solid which precipitates
  3. filtrationis filtered
  4. customrecrystallized twice from chloroform-acetone

Sources & evidence

ORD record
ord-322c5b6d2baa4ffeb79c1bb2efc2ebb8
Source dataset
uspto-grants-1976_09
Patent number
US03983124

Reaction notes

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