Bromomethyl 4-methoxyphenyl ketone → N-benzyl-4-(p-methoxybenzoylmethyl)-4-piperidinol hydrobromide

HRID 1888082Notes

Reaction equation

HRID 1888082 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[I-].[Na+].[Br:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:10].[CH2:19]([N:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Br.C(O)C>O1CCCC1>[BrH:7].[CH2:19]([N:26]1[CH2:31][CH2:30][C:29]([CH2:8][C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)([OH:32])[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 5238Sodium IodideHCID 192201-Benzyl-4-piperidoneHCID 24636Cerium(III) chlorideHCID 23002992HCID 23002992, compound

Product 1

HCID 67119971N-benzyl-4-(p-methoxybenzoylmethyl)-4-piperidinol hydrobromideYield 36.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous cerium chloride (0.99 g, 4.0 mmol) and sodium iodide (1.8 g, 12.0 mmol) are added to 10 ml of anhydrous tetrahydrofuran as a solvent to form a suspension. Dissolving 0.92 g (4.0 mmol) of 2-bromo-1-(4-methoxyphenyl)-ethanone and 0.76 g (4.0 mmol) of N-benzyl-4-piperidone in 10 ml of anhydrous tetrahydrofuran, and the solution is added dropwise to the above suspension and reacting at room temperature for 2 hours. Operating according to the post-treatment procedure in General Method three, and a salt is formed by acidifying with hydrobromic acid/ethanol solution, which is recrystallized in ethyl acetate/ethanol to obtain 0.61 g of a white crystal, with yield of 34.9%.

Workup

  1. customto form a suspension
  2. additionthe solution is added dropwise to the above suspension
  3. customa salt is formed
  4. customis recrystallized in ethyl acetate/ethanol

Sources & evidence

ORD record
ord-10826c0783e14e8aad4c696c72ebe726
Source dataset
uspto-grants-2013_08
Patent number
US08501778B2

Reaction notes

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