Hydrochloric Acid → o-Carbamoyl-alpha-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide monohydrochloride monohydrate

HRID 1381198Notes

Reaction equation

HRID 1381198 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[NH:6][C:7](=[O:15])[CH2:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)(=[O:3])[NH2:2].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[C:25]([Cl:27])=[O:26].Cl.Cl.C(O)C>C(Cl)Cl.C(N(CC)CC)C>[OH2:3].[ClH:27].[C:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[NH:6][C:7](=[O:15])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:22]([O:21][CH3:20])[CH:23]=2)[CH2:11][CH2:10]1)(=[O:3])[NH2:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77070Veratroyl chlorideHCID 13646249o-Carbamoyl-alpha-(1-piperazinyl)acetanilideHCID 21887872Ethanol hydrochloride

Product 1

HCID 23323531o-Carbamoyl-alpha-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide monohydrochloride monohydrate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

6.15 Grams of o-carbamoyl-α-(1-piperazinyl)acetanilide and 2.4 g of triethylamine were dissolved in 50 ml of methylene chloride, then to this solution was added dropwise a methylene chloride solution of 5.4 g of 3,4-dimethoxybenzoyl chloride under ice-cooled condition with stirring. The reaction was carried out at the same temperature for 1 hour, then the reaction mixture was washed with water, 5%-sodium bicarbonate aqueous solution, and an aqueous solution of potassium carbonate, then dried. Methylene chloride was removed by distillation, the residue was purified by a silica gel column chromatography, the product obtained was converted into a hydrochloride by adding hydrochloric acid-ethanol, then recrystallized from water-acetone to obtain 5.1 g of o-carbamoyl-α-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide monohydrochloride monohydrate in the form of colorless needle-like crystals. Melting point: 122.0°-125.0° C. (decomposed).

Workup

  1. temperaturecooled condition
  2. washthe reaction mixture was washed with water, 5%-sodium bicarbonate aqueous solution
  3. dry with materialan aqueous solution of potassium carbonate, then dried
  4. customMethylene chloride was removed by distillation
  5. customthe residue was purified by a silica gel column chromatography
  6. customthe product obtained
  7. customrecrystallized from water-acetone

Sources & evidence

ORD record
ord-00d273adfece4b1690b591384941da89
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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