Hydrochloric Acid → N-{1-[4-(3,4-Dichlorophenoxy)-piperidin-1-ylmethyl]-2-methyl-propyl}-4-methyl-benzamide, hydrochloride

HRID 496884Notes

Reaction equation

HRID 496884 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:13]([NH2:17])[CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1.[CH3:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+].Cl>ClCCl.C(OCC)(=O)C.C(N(CC)CC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH:13]([NH:17][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][C:23]([CH3:22])=[CH:24][CH:25]=2)[CH:14]([CH3:15])[CH3:16])[CH2:10][CH2:11]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 134054-Methylbenzoyl ChlorideHCID 516892Sodium BicarbonateHCID 537589381-[4-(3,4-Dichlorophenoxy)-piperidin-1-ylmethyl]-2-methyl-propylamine

Product 1

HCID 131725155N-{1-[4-(3,4-Dichlorophenoxy)-piperidin-1-ylmethyl]-2-methyl-propyl}-4-methyl-benzamide, hydrochloride

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of step (iii) (0.2 g) was dissolved in dichloromethane (5 ml), triethylamine (0.126 ml) and 4-methylbenzoyl chloride (0.097 ml) were added. After 2 hours at room temperature, ethyl acetate and aqueous NaHCO3 solution were added, the organic phase separated and the solvent removed to leave an oil. Purification by reverse phase HPLC (with a gradient eluent system (25% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)) gave a gum. Addition of 1.0M ethereal hydrogen chloride solution gave the titled product as a solid (0.104 g).

Workup

  1. customthe organic phase separated
  2. customthe solvent removed
  3. customto leave an oil
  4. customPurification by reverse phase HPLC (with a gradient eluent system (25% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%))
  5. customgave a gum

Sources & evidence

ORD record
ord-54ede5879a9243c1bfd3f63c0cb3261b
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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