Chloroacetyl chloride → HCID 19030793, compound

HRID 266803Notes

Reaction equation

HRID 266803 reaction equation
[CH3:1][NH:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][C:16]3=[O:17])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[Cl:28][CH2:29][C:30](Cl)=[O:31].C(N(CC)CC)C>ClCCl>[Cl:28][CH2:29][C:30]([N:2]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][C:16]3=[O:17])[CH2:11][CH2:10]2)=[O:8])=[CH:26][CH:27]=1)[CH3:1])=[O:31]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 19030851HCID 19030851, compound

Product 1

HCID 19030793HCID 19030793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-{1-[4-(N-methylamino)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (200 mg) is dissolved in dichloromethane (5 ml) and thereto is added α-chloroacetyl chloride (55 μl) under ice cooling. Continually thereto is added triethylamine (0.23 ml) and the mixture is stirred at room temperature overnight. After the solvent is concentrated, the residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) and recrystallized from n-hexane/ethanol to give 1-{1-[4-(N-α-chloroacetyl-N-methylamino)benzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (0.18 g) as white powder, m.p.: 220°-222° C. (decomposed).

Workup

  1. concentrationAfter the solvent is concentrated
  2. customthe residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)
  3. customrecrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-cb8870b09115415087f976728b2a21e0
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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