Chloroacetyl chloride → HCID 9807390, compound

HRID 1975345Notes

Reaction equation

HRID 1975345 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][N:7]([C:15]1[CH:37]=[CH:36][C:18]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[CH2:23][CH2:22]2)=[O:20])=[CH:17][CH:16]=1)[C:8]([O:10]C(C)(C)C)=O)([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Cl:44][CH2:45]C(Cl)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[ClH:35].[CH:1]([O:4][CH2:5][CH2:6][N:7]([C:15]1[CH:37]=[CH:36][C:18]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)[CH2:23][CH2:22]2)=[O:20])=[CH:17][CH:16]=1)[C:8](=[O:10])[CH2:45][Cl:44])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 19099473HCID 19099473, compound

Product 1

HCID 9807390HCID 9807390, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

22 g of 1-{4-[N-(2-isopropyloxyethyl)amino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine (Example 2) and 20.7 g of potash are introduced into 650 ml of toluene, and the mixture is kept at 45° for 15 minutes. At that temperature and with stirring, a solution of 7.1 g of chloroacetyl chloride in 30 ml of toluene is added dropwise. The mixture is stirred for 30 minutes at 45° and then stirring is continued at room temperature. The reaction solution is diluted with 500 ml of ethyl acetate and washed twice with 250 ml of water each time. The oil obtained after concentration by evaporation is chromatographed over silica gel and recrystallised in the form of the hydrochloride from acetone/ether, yielding 1-{4-[N-(2-isopropyloxyethyl)-N-chloroacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point of 146°-147°.

Workup

  1. stirringThe mixture is stirred for 30 minutes at 45°
  2. stirringstirring
  3. customis continued at room temperature
  4. washwashed twice with 250 ml of water each time
  5. customThe oil obtained
  6. concentrationafter concentration
  7. customby evaporation
  8. customis chromatographed over silica gel
  9. customrecrystallised in the form of the hydrochloride from acetone/ether

Sources & evidence

ORD record
ord-5e481a0a04834e0f8d33f75559841784
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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