Piperazine → 1-(4-methyl-3-nitrophenyl)-2-(piperazin-1-yl)-1H-indole-3-carboxaldehyde

HRID 1678178Notes

Reaction equation

HRID 1678178 reaction equation
Cl[C:2]1[N:3]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]([CH:11]=[O:12])=[C:2]2[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 860359152-chloro-1-(4-methyl-3-nitrophenyl)-1H-indole-3-carboxaldehyde

Product 1

HCID 113374791-(4-methyl-3-nitrophenyl)-2-(piperazin-1-yl)-1H-indole-3-carboxaldehydeYield 68%

Procedure

2-chloro-1-(4-methyl-3-nitrophenyl)-1H-indole-3-carboxaldehyde is reacted with piperazine as described in Step 2 of Example 29 to afford 1-(4-methyl-3-nitrophenyl)-2-(piperazin-1-yl)-1H-indole-3-carboxaldehyde (68% yield). ESI/MS 365 (M+H); RT=2.65 min; NMR (CDCl3) 10.35 (1H, s); 8.31 (1H, d, J=9 Hz); 8.11 (1H, s); 7.61 (2H); 7.31 (2H); 7.01 (1H, d, J=9 Hz); 3.31 (4H, m); 2.88 (4H, m); 2.74 (3H, s).

Sources & evidence

ORD record
ord-bc181035354847de9d49dfe58c0d534b
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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