Sodium Iodide → N-benzyl-4-(p-chlorobenzoylmethyl)-4-piperidinol hydrobromide

HRID 1888083Notes

Reaction equation

HRID 1888083 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[I-].[Na+].[Br:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:10].[CH2:18]([N:25]1[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Br.C(O)C>O1CCCC1>[BrH:7].[CH2:18]([N:25]1[CH2:30][CH2:29][C:28]([CH2:8][C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)([OH:31])[CH2:27][CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 192201-Benzyl-4-piperidoneHCID 24636Cerium(III) chlorideHCID 68303p-Chlorophenacyl bromideHCID 23002992HCID 23002992, compound

Product 1

HCID 67119853N-benzyl-4-(p-chlorobenzoylmethyl)-4-piperidinol hydrobromideYield 38.3%

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 0.98 g (4.0 mmol) of 2-bromo-1-(4-chlorophenyl)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 ethanol to obtain 0.65 g of a white crystal, with yield of 36.7%.

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 ethanol

Sources & evidence

ORD record
ord-53ceed6c4d7b43dd9a3a453005414ec8
Source dataset
uspto-grants-2013_08
Patent number
US08501778B2

Reaction notes

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