Chloroacetyl chloride → HCID 19099487, compound

HRID 1975375Notes

Reaction equation

HRID 1975375 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:9]=[C:10]([CH:28]=[CH:29][CH:30]=1)[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:15][CH2:14]1)=[O:12])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[Cl:40][CH2:41][C:42](Cl)=[O:43]>O1CCCC1>[ClH:27].[CH:1]([O:4][CH2:5][CH2:6][N:7]([C:8]1[CH:9]=[C:10]([CH:28]=[CH:29][CH:30]=1)[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[CH2:15][CH2:14]1)=[O:12])[C:42](=[O:43])[CH2:41][Cl:40])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 19099455HCID 19099455, compound

Product 1

HCID 19099487HCID 19099487, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.77 g of 1-[3-(2-isopropyloxyethylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine are dissolved in 50 ml of absolute tetrahydrofuran and stirred at RT with 1.07 g of Hunig base and 0.794 g of chloroacetyl chloride in 5 ml of absolute tetrahydrofuran. After approximately 15 minutes, the thin suspension is concentrated by evaporation, dissolved in ethyl acetate and washed with water until neutral. Concentration by evaporation, chromatography of the residue over silica gel (eluant: ethyl acetate) and treatment with ethereal hydrochloric acid yield 1-{3-[N-(2-isopropyloxyethyl)-N-chloroacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point of 115°-117°.

Workup

  1. concentrationthe thin suspension is concentrated by evaporation
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water until neutral
  4. concentrationConcentration
  5. customby evaporation, chromatography of the residue over silica gel (eluant: ethyl acetate) and treatment with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-052b9323ef9641a79c460e021396d041
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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