1-Benzyl-4-piperidone → N-t-butoxycarbonyl-4-[(1-benzyl-4-hydroxypiperidin-4-yl)acetyl]aniline

HRID 976149Notes

Reaction equation

HRID 976149 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.CCCCC.[CH2:28]([N:35]1[CH2:40][CH2:39][C:38](=[O:41])[CH2:37][CH2:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH2:16][C:38]2([OH:41])[CH2:39][CH2:40][N:35]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:36][CH2:37]2)=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 15373979tert-Butyl (4-acetylphenyl)carbamateHCID 178446069HCID 178446069, compound

Product 1

HCID 19968906N-t-butoxycarbonyl-4-[(1-benzyl-4-hydroxypiperidin-4-yl)acetyl]anilineYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

30 ml of tetrahydrofuran was added to 2.00 g of N-t-butoxycarbonyl-4-acetylaniline, and 8.8 ml of a 1.7M t-butyl lithium·pentane solution was added thereto under an argon stream at -78° C. Then, 1.41 g of 1-benzyl-4-piperidone was dissolved in 20 ml of tetrahydrofuran, and the solution was added dropwise. After stirring for 2 hours, a saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the obtained residue was applied to silica gel column chromatography to obtain 2.07 g of the title compound as white powder.

Workup

  1. additionwas added
  2. customat -78° C
  3. additionthe solution was added dropwise
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-9defd28aaa69446d8e4abf7af16a5a38
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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