Hydrochloric Acid → N-{2-[4-(3,4-Dichlorobenzoyl)-1-piperazinyl]ethyl}-3-methoxybenzamide hydrochloride

HRID 496881Notes

Reaction equation

HRID 496881 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)=[O:18])[CH2:13][CH2:12]1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](Cl)=[O:33].O.Cl>N1C=CC=CC=1.C(OCC)(=O)C>[ClH:25].[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[C:17]([N:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:8][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][CH:37]=[C:29]([O:28][CH3:27])[CH:30]=2)[CH2:12][CH2:13]1)=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 74374m-Anisoyl chlorideHCID 22322358[4-(2-Aminoethyl)-1-piperazinyl](3,4-dichlorophenyl)methanone trifluoroacetate

Product 1

HCID 22322220N-{2-[4-(3,4-Dichlorobenzoyl)-1-piperazinyl]ethyl}-3-methoxybenzamide hydrochloride

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from step (iii) above (0.15 g) was dissolved in pyridine (2 ml) and 3-methoxybenzoyl chloride (0.064 g) added. After 16 hours at room temperature, water and ethyl acetate were added, the organic phase separated, dried and concentrated to an oil. Purification by chromatography (dichloromethane:methanol, 95:5) gave an oil which was treated with 1.0M ethereal hydrogen chloride solution to give the titled product as a solid (0.043 g).

Workup

  1. customthe organic phase separated
  2. customdried
  3. concentrationconcentrated to an oil
  4. customPurification by chromatography (dichloromethane:methanol, 95:5)
  5. customgave an oil which

Sources & evidence

ORD record
ord-5e33559530ca46df8cd36c8e169be893
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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