Piperidine → HCID 345229, compound

HRID 276153Notes

Reaction equation

HRID 276153 reaction equation
[C:1]1([C:7]2[O:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:11]=2Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.CC([O-])(C)C.[K+].[Cl-].[Li+]>C1COCC1>[C:1]1([C:7]2[O:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:11]=2[N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 433294Lithium ChlorideHCID 458246HCID 458246, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 345229HCID 345229, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 mmol of 2,5-diphenyl-3-chlorofuran (7.64 g), 32 mmol of freshly distilled piperidine (3.0 g), 32 mmol of KOtBu (3.6 g), 2 mmol of lithium chloride (42.5 mg) and 44 mg of trans-di-μ-acetatobis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]dipalladium(II) (0.2 mol %) are suspended in 50 ml of THF and placed in a pressure tube under protective gas. After 12 hours at 110° C., the tube is cooled to room temperature, the salts are filtered off and washed with petroleum ether. The solvents are removed from the filtrate on a rotary evaporator. Crystallization from 96% strength ethanol gives 2,5-diphenyl-3-piperidinofuran as a colorless solid; yield: 84%; melting point: 103° C.

Workup

  1. customplaced in a pressure tube under protective gas
  2. filtrationthe salts are filtered off
  3. washwashed with petroleum ether
  4. customThe solvents are removed from the filtrate on a rotary evaporator
  5. customCrystallization from 96% strength ethanol

Sources & evidence

ORD record
ord-c60bb8a4dd934a0a949c6ec3b254297a
Source dataset
uspto-grants-2002_03
Patent number
US06353136B1

Reaction notes

Loading…