1-Phenylpiperazine → 2-{3-[4-(4-fluorobenzoyl)-piperidin-1-yl]-propyl}-6,7-dimethoxy-1(2H)-phthalazinone hydrochloride

HRID 703455Notes

Reaction equation

HRID 703455 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[N:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[C:5]1=[O:18].ClCC[CH2:22][N:23]1N=C[C:30]2[C:25](=CC(OC)=[C:28](OC)[CH:29]=2)[C:24]1=O.C1(N2CCNCC2)C=CC=CC=1.[F:50][C:51]1[CH:64]=[CH:63][C:54]([C:55](N2CCNCC2)=[O:56])=[CH:53][CH:52]=1>C(OCC)(=O)C>[ClH:1].[F:50][C:51]1[CH:52]=[CH:53][C:54]([C:55]([CH:30]2[CH2:25][CH2:24][N:23]([CH2:22][CH2:2][CH2:3][N:4]3[N:13]=[CH:12][C:11]4[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=4)[C:5]3=[O:18])[CH2:28][CH2:29]2)=[O:56])=[CH:63][CH:64]=1

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 771862(4-Fluorophenyl)(piperazin-1-yl)methanoneHCID 153919232-(2-chloroethyl)-6,7-dimethoxy-1(2H)-phthalazinoneHCID 221501712-(3-chloropropyl)-6,7-dimethoxy-1(2H)-phthalazinone

Product 1

HCID 221501482-{3-[4-(4-fluorobenzoyl)-piperidin-1-yl]-propyl}-6,7-dimethoxy-1(2H)-phthalazinone hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Working as described in Example 3 but replacing 2-(2-chloroethyl)-6,7-dimethoxy-1(2H)-phthalazinone with an equivalent amount of 2-(3-chloropropyl)-6,7-dimethoxy-1(2H)-phthalazinone obtained as described in Example 13, and replacing N-phenylpiperazine with an equivalent amount of 4-(4-fluorobenzoyl)-piperazine, 2-{3-[4-(4-fluorobenzoyl)-piperidin-1-yl]-propyl}-6,7-dimethoxy-1(2H)-phthalazinone hydrochloride is obtained (m.p. 250°-252° C., from ethyl acetate).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-d4ca02ec99a4431e93c2d9d564da5b07
Source dataset
uspto-grants-1991_01
Patent number
US04983606

Reaction notes

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