2-chloro-1-phenyl-1H-indole-3-carbaldehyde → 4-(3-formyl-1-phenyl-1H-indole-2-yl)-piperazine-2-carboxylic acid methyl ester

HRID 751362Notes

Reaction equation

HRID 751362 reaction equation
Cl[C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:19][O:20][C:21]([CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1)=[O:22]>>[CH3:19][O:20][C:21]([CH:23]1[CH2:28][N:27]([C:2]2[N:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]3[C:9]([C:10]=2[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:26][CH2:25][NH:24]1)=[O:22]

Participants

3

Reactant 2

HCID 3147932-chloro-1-phenyl-1H-indole-3-carbaldehydeHCID 2760426Methyl Piperazine-2-carboxylate

Product 1

HCID 117399914-(3-formyl-1-phenyl-1H-indole-2-yl)-piperazine-2-carboxylic acid methyl esterYield 9%

Procedure

2-Chloro-1-phenyl-1H-indole-3-carboxaldehyde is reacted with piperazine-2-carboxylic acid methyl ester as described in Example 1 to afford 4-(3-formyl-1-phenyl-1H-indole-2-yl)-piperazine-2-carboxylic acid methyl ester (9% yield) as a yellow solid. LC/MS: MS 364 (M+H); RT 2.54 min; NMR (CDCl3): 10.29 (1H, s), 8.26 (1H, d), 7.07-7.65 (m, buried), 6.98 (1H, d), 3.60-4.10 (4H, m), 2.60-3.55 (6H, m).

Sources & evidence

ORD record
ord-729c173c43c04ae48ce61ac5cde8916d
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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