tert-Butyl piperazine-1-carboxylate → HCID 11328687, compound

HRID 751376Notes

Reaction equation

HRID 751376 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH:20]=[O:21])=[C:12]2Cl)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:23]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>>[C:26]([O:25][C:23]([N:30]1[CH2:35][CH2:34][N:33]([C:12]2[N:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=3)[C:19]3[C:14]([C:13]=2[CH:20]=[O:21])=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:32][CH2:31]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 860359201-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde

Product 1

HCID 11328687HCID 11328687, compoundYield 70%

Procedure

1-(4-tert-Butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde is reacted with 1-Boc-piperazine as described in Step 2 of Example 29 to afford 4-[1-(4-tert-butylphenyl)-3-formyl-1H-indol-2-yl]piperazine-1-carboxylic acid tert-butyl ester (70% yield) as a light yellow solid. TLC (heptane-30% ethyl acetate) Rf 0.19; ESI/MS 462 (M+H); RT=4.42 min.; NMR10.13 (1H, s); 8.13 (1H, d, J=9 Hz); 7.68 (2H, d); 7.49 (2H, d); 7.21 (2H, m); 6.95 (1H, d, J=9 Hz); 3.20 (8H, m); 1.37 (18H, s).

Sources & evidence

ORD record
ord-cd3309e7923f476695940e2d9243d66f
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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