Sodium Hydroxide → HCID 13477818, compound

HRID 371087Notes

Reaction equation

HRID 371087 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].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[CH2:26]Cl>[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]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:23]([O:22][CH3:21])[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 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 4353582HCID 4353582, compound

Product 1

HCID 13477818HCID 13477818, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.8 g of 50% aqueous sodium hydroxide solution, 5 ml of methylene chloride, 1 g (0.004 mol) of 1-(4-nitrobenzoyl)-4-hydroxypiperidine, 1.30 g (0.006 mol) of 3,4,5-trimethoxybenzyl chloride and 0.08 g (2×10-4 mol) of tetrabutylammonium iodide is stirred for 5 hours at 50° C. After dilution with 10 ml of water and 15 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 1.36 g (79%) of a product which is purified by dissolving it in 7 ml of DMF and slowly reprecipitating it with 7 ml of water. After washing with water and drying in vacuo, 1-(4-nitrobenzoyl)-4-(3,4,5-trimethoxybenzyloxy)-piperidine, m.p. 124° C., is obtained.

Workup

  1. customAfter dilution with 10 ml of water and 15 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 1.36 g (79%) of a product which is purified
  9. dissolutionby dissolving it in 7 ml of DMF
  10. customslowly reprecipitating it with 7 ml of water
  11. washAfter washing with water
  12. dry with materialdrying in vacuo, 1-(4-nitrobenzoyl)-4-(3,4,5-trimethoxybenzyloxy)-piperidine, m.p. 124° C.
  13. customis obtained

Sources & evidence

ORD record
ord-e139cc43f01d403195ac30fcaf03a223
Source dataset
uspto-grants-1985_07
Patent number
US04529730

Reaction notes

Loading…