Sodium Hydroxide → [4-[(4-Fluorophenyl)methoxy]-1-piperidinyl](4-nitrophenyl)methanone

HRID 371086Notes

Reaction equation

HRID 371086 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:20]=[CH:19][C:9]([C:10]([N:12]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[N+:3]([C:6]1[CH:20]=[CH:19][C:9]([C:10]([N:12]2[CH2:13][CH2:14][CH:15]([O:18][CH2:26][C:25]3[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=3)[CH2:16][CH2:17]2)=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 4353582HCID 4353582, compound

Product 1

HCID 12796402[4-[(4-Fluorophenyl)methoxy]-1-piperidinyl](4-nitrophenyl)methanone

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.6 g of a 50% aqueous sodium hydroxide solution, 10 ml of methylene chloride, 2 g (0.008 mol) of 1-(4-nitrobenzoyl)-4-hydroxypiperidine, 2.32 g (0.012 mol) of 4-fluorobenzyl bromide and 0.15 g (4×10-4 mol) of tetrabutylammonium iodide is stirred for 5 hours at 50° C. After dilution of the reaction medium with 20 ml of water and 30 ml of methylene chloride, the organic phase is decanted, washed with water until the washings are neutral, dried (MgSO4) and evaporated in vacuo. The residual oil obtained crystallises on stirring in diethyl ether. This yields 2.23 g of a product which is purified by dissolving it in 11 ml of dimethylformamide (DMF) and reprecipitating it by the dropwise addition of 11 ml of water, whilst stirring. After washing with water and drying in vacuo, 1-(4-nitrobenzoyl)-4-(4-fluorobenzyloxy)-piperidine, m.p. 120° C., is obtained.

Workup

  1. customAfter dilution of the reaction medium with 20 ml of water and 30 ml of methylene chloride, the organic phase is decanted
  2. washwashed with water until the washings
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residual oil obtained
  6. customcrystallises
  7. stirringon stirring in diethyl ether
  8. customThis yields 2.23 g of a product which is purified
  9. dissolutionby dissolving it in 11 ml of dimethylformamide (DMF)
  10. customreprecipitating it
  11. additionby the dropwise addition of 11 ml of water
  12. stirringwhilst stirring
  13. washAfter washing with water
  14. dry with materialdrying in vacuo, 1-(4-nitrobenzoyl)-4-(4-fluorobenzyloxy)-piperidine, m.p. 120° C.
  15. customis obtained

Sources & evidence

ORD record
ord-1665e01d201b41cd8ecf6f7abdef9fe5
Source dataset
uspto-grants-1985_07
Patent number
US04529730

Reaction notes

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