Aluminium lithium hydride → HCID 67388896, compound

HRID 269829Notes

Reaction equation

HRID 269829 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](=O)[CH2:9][CH:10]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[C:11](=O)[N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH:10]([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=2)[CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 673885181-Methyl-4-[3-(4-nitrophenyl)-4-oxo-4-piperidin-1-ylbutanoyl]piperazine

Product 1

HCID 67388896HCID 67388896, compound

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-e49c6916b3fd483bbf15ea2459680783
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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