tert-Butyl piperazine-1-carboxylate → HCID 11188928, compound

HRID 751379Notes

Reaction equation

HRID 751379 reaction equation
Cl[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:2]2[N:3]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:4]3[C:9]([C:10]=2[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 11188928HCID 11188928, compoundYield 43%

Procedure

2-Chloro-1H-indole-3-carboxaldehyde is reacted with t-butyl-1-piperazinecarboxylate as described in Step 2 of Example 29 to afford 4-(3-formyl-1-phenyl-1H-indol-2-yl)piperazine-1-carboxylic acid tert-butyl ester (43% yield) as a yellow solid. ESI/MS 300 (M), 306 [M-CO2C(CH3)3], 350 [M-C(CH3)3], 406 (M+H); RT=3.89 min; NMR 10.15 (1H, s); 8.14 (1H, d, J=9 Hz); 7.69 (5H, m); 7.22 (2H, m); 6.94 (1H, d, J=9 Hz); 3.22 (8H, 2 br m); 1.37 (9H, s).

Sources & evidence

ORD record
ord-13c7d64f9eb94da7be544472933cd2b3
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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