Hydrochloric Acid → 6-{3-[4-(4-chlorophenylmethyl)-1-piperazinyl]-propoxy}-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-one

HRID 22328Notes

Reaction equation

HRID 22328 reaction equation
[OH:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]2[O:10][C:9](=[O:11])[C:8]([CH3:12])=[C:7]([CH3:13])[C:6]=2[CH:14]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33]Cl)[CH2:27][CH2:26]2)=[CH:20][CH:19]=1.C(O)(C)C.Cl>O>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][N:25]2[CH2:26][CH2:27][N:28]([CH2:31][CH2:32][CH2:33][O:1][C:2]3[C:3]([O:15][CH3:16])=[CH:4][C:5]4[O:10][C:9](=[O:11])[C:8]([CH3:12])=[C:7]([CH3:13])[C:6]=4[CH:14]=3)[CH2:29][CH2:30]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776Isopropanol2×HCID 133997271-[(4-Chlorophenyl)methyl]-4-(3-chloropropyl)piperazineHCID 199277156-hydroxy-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-one

Product 1

HCID 199276756-{3-[4-(4-chlorophenylmethyl)-1-piperazinyl]-propoxy}-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-oneYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Method D (5 h at 90° C.); starting materials: 6-hydroxy-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-one (example 103) and 1-[(4-chlorophenyl)methyl]-4-(3-chloropropyl)piperazine; yield: 74%; fusion point 96°-97° C. (from isopropanol and petroleum ether). Hydrochloride (x 2 HCl): method G; yield 95%; fusion point 255°-260° C. (from isopropanol and water).

Workup

  1. customMethod D (5 h at 90° C.)

Sources & evidence

ORD record
ord-a4995629b6204d468d5b4336e14f9897
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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