4-Chlorobenzoyl chloride → 7-(4-Chlorobenzoyloxy)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235140Notes

Reaction equation

HRID 235140 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 85014-Chlorobenzoyl chloride2×HCID 108002178-(4-Methylpiperazin-1-yl)naphthalen-2-ol

Product 1

HCID 189675097-(4-Chlorobenzoyloxy)-1-(4-methyl-1-piperazinyl)-naphthalene

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The title product was obtained following the procedure of example 30 from 7-hydroxy-1-(4-methyl-1-piperazinyl)-naphthalene (0.065 g, 0.268 mmol) and 4-chlorobenzoyl chloride (0.035 mL, 0.275 mmol) in methylene chloride (1 mL) and saturated sodium bicarbonate (1 mL) with a second equivalent of 4-chlorobenzoyl chloride added after several hours of stirring at room temperature. The title product was obtained in a yield of 0.058 g (57%) after recrystallization from ether/hexane: mp 110°-111 ° C. Analysis calculated for C22H21ClN2O2 : C, 69.38; H, 5.56; N, 7.36. Found: C, 69.31; H, 5.61; N, 7.35.

Workup

  1. additionadded after several hours

Sources & evidence

ORD record
ord-da4ff06fa87345d691173d4446914752
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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