Cyclohexanone → 4-(1H-Indol-5-yl)-1-methylpiperidin-4-ol

HRID 411970Notes

Reaction equation

HRID 411970 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3([OH:16])[CH2:15][CH2:14]C[CH2:12][CH2:11]3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.BrC1C=C2C(=CC=1)[NH:23][CH:22]=C2.[Li]C(C)(C)C.CCCCC.C1(=O)CCCCC1>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3([OH:16])[CH2:15][CH2:14][N:23]([CH3:22])[CH2:12][CH2:11]3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 5

HCID 7967CyclohexanoneHCID 8003PentaneHCID 249055-BromoindoleHCID 185347811-(1H-Indol-5-yl)cyclohexanolHCID 178418306HCID 178418306, compound

Product 1

HCID 185347794-(1H-Indol-5-yl)-1-methylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(1H-Indol-5-yl)cyclohexanol (1.95g 35%): from 5-bromo-1H-indole (5 g, 25.5 mmol) with KH (1.127 g, 28.1 mmol) in THF at −10° C., then treated with 1.7 M t-BuLi in pentane (37.5 mL, 63.8 mmol) and cyclohexanone (5.68 mL, 54.8 mmol) at −78° C.

Sources & evidence

ORD record
ord-f738aec1916a4626be2d364e3d12118e
Source dataset
uspto-grants-2003_05
Patent number
US06562809B1

Reaction notes

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