Piperidine → HCID 21392946, compound

HRID 461962Notes

Reaction equation

HRID 461962 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([C:18](=[O:21])[CH2:19]Cl)=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)=[O:4].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[ClH:1].[ClH:1].[N:22]1([CH2:2][C:3]([C:5]2[CH:17]=[CH:16][C:15]3[C:14]4[C:9](=[CH:10][C:11]([C:18](=[O:21])[CH2:19][N:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:12][CH:13]=4)[CH2:8][C:7]=3[CH:6]=2)=[O:4])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10340Sodium CarbonateHCID 21392981HCID 21392981, compound

Product 1

HCID 21392946HCID 21392946, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 19.0g (0.06 mole) of 2,7-bis(chloroacetyl)fluorene, 10.2g (0.12 mole) of piperidine and 25.4g (0.24 mole) of sodium carbonate in 300 ml of tetrahydrofuran was gently refluxed with stirring for 36 hours then filtered and concentrated in vacuo. The residue was extracted with ether and this solution was treated with ethereal hydrogen chloride to give the desired product which was recrystallized from methanol-butanone-ether. M.P. 302°-304° C (dec.), λmaxH2O 337, E1cm1% 834.

Workup

  1. temperaturewas gently refluxed
  2. filtrationthen filtered
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ether
  5. additionthis solution was treated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-3d1833fd93bf46e3862b7ac5030e4d00
Source dataset
uspto-grants-1977_12
Patent number
US04064347

Reaction notes

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