Hydrochloric Acid → o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

HRID 1381193Notes

Reaction equation

HRID 1381193 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:4].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22].Cl.C(N(CC)CC)C>C(#N)C>[CH3:11][O:10][C:8]([C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:26]1[CH2:27][CH2:28][N:23]([C:21](=[O:22])[C:20]2[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:18]([O:17][CH3:16])[CH:19]=2)[CH2:24][CH2:25]1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 295954Methyl 2-[(chloroacetyl)amino]benzoateHCID 8734071-(3,4-Dimethoxybenzoyl)piperazine

Product 1

HCID 13117363o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.06 Grams of methyl o-(α-chloroacetylamino)benzoate, 15.2 g of N-(3,4-dimethoxybenzoyl)piperzine.monohydrochloride and 16 g of triethylamine were suspended in 55 ml of acetonitrile, and the mixture was reacted at 49°-50° C. for 4 hours. After completion of the reaction, the reaction mixture was ice-cooled, and the crystals formed were collected by filtration. Recrystallized from ethanol to obtain 14.68 g of o-methoxycarbonyl-α-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide in the form of colorless needle-like crystals. Melting point: 167.5°-169.0° C.

Workup

  1. customthe mixture was reacted at 49°-50° C. for 4 hours
  2. customAfter completion of the reaction
  3. temperaturecooled
  4. customthe crystals formed
  5. filtrationwere collected by filtration
  6. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-77c1863b064043ecae1518fa1df2e8d8
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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