tert-butyl 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylate → 5-chloro-3-(piperidin-4-yl)-1H-indole hydrochloride

HRID 58661Notes

Reaction equation

HRID 58661 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1>Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 12072033tert-butyl 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylate

Product 1

HCID 203455215-chloro-3-(piperidin-4-yl)-1H-indole hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl 4-(5-chloro-1H-indol-3-yl)piperidine-1-carboxylate (1 g; 2.99 mmol) was dissolved in 7.5 mL of a 4M solution of HCl in dioxane. The mixture was stirred at room temperature for 2 hours and was concentrated under reduced pressure to give quantitatively 5-chloro-3-(piperidin-4-yl)-1H-indole hydrochloride as a solid.

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-0fe0be036c7a41ae863ed6512e450b3c
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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