Hydrochloric Acid → N-{1-[4-(3,4-dichlorobenzoyl)-piperidin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide

HRID 369931Notes

Reaction equation

HRID 369931 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH:21]([NH:25][C:26](=[O:34])[C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)[CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]3)OCC[O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[C:9]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH:21]([NH:25][C:26](=[O:34])[C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)[CH:22]([CH3:23])[CH3:24])[CH2:16][CH2:15]1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23283153N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide

Product 1

HCID 9912127N-{1-[4-(3,4-dichlorobenzoyl)-piperidin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide (0.4 g, 0.791 mmol), aqueous HCl (10 mL, 6 N), and acetonitrile (10 mL) was refluxed for 2 h. After concentrating the reaction mixture, the residue was stirred with ethyl acetate and water. Sodium hydroxide solution (6 N) was added until the aqueous layer was pH 8. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over magnesium sulfate and concentrated to give N-{1-[4-(3,4-dichlorobenzoyl)-piperidin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide which was converted to the hydrochloride salt by adding 2 molar excess ethereal HCl (1 M) to an ether solution of the free base.

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationAfter concentrating the reaction mixture
  3. additionSodium hydroxide solution (6 N) was added until the aqueous layer
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organics were dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ccfe8d7218344c2d86889fa49f3bc49f
Source dataset
uspto-grants-2000_10
Patent number
US06140344

Reaction notes

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