6,7-Dichloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl chloride → 1-(6,7-Dichloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl)-4-methyl-2-(pyrrolidin-1-ylmethyl)piperazine dihydrochloride

HRID 1292434Notes

Reaction equation

HRID 1292434 reaction equation
[ClH:1].Cl.Cl.[CH3:4][N:5]1[CH2:10][CH2:9][NH:8][CH:7]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:6]1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[Cl:28])[CH:24]([C:29](Cl)=[O:30])[CH2:23][CH2:22][C:21]2=[O:32]>C(N(CC)CC)C>[ClH:17].[ClH:1].[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[Cl:28])[CH:24]([C:29]([N:8]1[CH2:9][CH2:10][N:5]([CH3:4])[CH2:6][CH:7]1[CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:30])[CH2:23][CH2:22][C:21]2=[O:32]

Participants

4

Reactant 2

HCID 153428716,7-Dichloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl chlorideHCID 189151091-Methyl-3-(pyrrolidin-1-ylmethyl)piperazine trihydrochloride

Product 1

HCID 189151301-(6,7-Dichloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl)-4-methyl-2-(pyrrolidin-1-ylmethyl)piperazine dihydrochlorideYield 108.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The procedure described in Example 24 was repeated, but using 1.0 g of 1-methyl-3-(pyrrolidin-1-ylmethyl)piperazine trihydrochloride, 2.1 ml of triethylamine and 1.0 g of 6,7-dichloro-1,2,3,4-tetrahydro-4-oxo-1-naphthoyl chloride, to afford 0.97 g of the title compound, melting at 275°-278° C. (dec.).

Sources & evidence

ORD record
ord-b4fc0747ff694592a845442080d8ffd0
Source dataset
uspto-grants-1998_05
Patent number
US05756730

Reaction notes

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