Sodium hydride → 1-{3-[4-(N-acetyl-N-(3-methyl-2-butenyl)-amino)-2-methoxyphenoxy]-n-propyl}-4-phenyl-piperazine

HRID 1648785Notes

Reaction equation

HRID 1648785 reaction equation
[C:1]([NH:4][C:5]1[CH:26]=[CH:25][C:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[C:7]([O:27][CH3:28])[CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:31][C:32]([CH3:36])=[CH:33][CH2:34]Br>CN(C)C=O>[C:1]([N:4]([C:5]1[CH:26]=[CH:25][C:8]([O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][CH2:18]2)=[C:7]([O:27][CH3:28])[CH:6]=1)[CH2:34][CH:33]=[C:32]([CH3:36])[CH3:31])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 12838122HCID 12838122, compound

Product 1

HCID 204817571-{3-[4-(N-acetyl-N-(3-methyl-2-butenyl)-amino)-2-methoxyphenoxy]-n-propyl}-4-phenyl-piperazineYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of 1-[3-(4- acetamido-2- methoxyphenoxy)-n-propyl]-4-phenyl-piperazine, 232 mg of 65% sodium hydride, 940 mg of 3-methyl-2- butenyl bromide and 60 ml of anhydrous dimethylformamide are treated in the same manner as described in Example 13. 1.78 g of 1-{3-[4-(N-acetyl-N-(3-methyl-2-butenyl)-amino)-2-methoxyphenoxy]-n-propyl}-4-phenyl-piperazine are thereby obtained as a pale yellow oil. Yield: 86.3%

Sources & evidence

ORD record
ord-ad8644db553b4e48af423cce2e6f4dc6
Source dataset
uspto-grants-1983_11
Patent number
US04413006

Reaction notes

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