Sodium Hydroxide → HCID 67388518, compound

HRID 905680Notes

Reaction equation

HRID 905680 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:20][C:21]([O:23]C)=O.[OH-].[Na+].[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>CO>[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:21](=[O:23])[CH2:20][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:11](=[O:12])[N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 60984Methyl bromoacetateHCID 35942761-[(4-Nitrophenyl)acetyl]piperidine

Product 1

HCID 67388518HCID 67388518, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(4-Nitrophenyl)acetyl]piperidine was alkylated with methyl bromoacetate in the same manner as in Reference Example 47, hydrolyzed with 1 M sodium hydroxide aqueous solution in methanol, and then condensed with 1-methylpiperazine in the same manner as in Reference Example 5 to obtain 1-methyl-4-[3-(4-nitrophenyl)-4-oxo-4-piperidin-1-ylbutanoyl]piperazine (ESI: 389). This piperazine compound was subjected to the reduction of nitro group in the same manner as the catalytic hydrogenation shown in Reference Example 3 and then treated with lithium aluminum hydride to obtain 4-[3-(4-methylpiperazin-1-yl)-1-(piperidin-1-ylmethyl)propyl]aniline. ESI: 331.

Sources & evidence

ORD record
ord-f9fadd94d5b44f6dac72f6f94a53c5f8
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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