Hydrochloric Acid → 4-(6-cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine hydrochloride

HRID 1969003Notes

Reaction equation

HRID 1969003 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=3)[CH2:16][C:15]2=[O:25])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[ClH:26].O1CCOCC1>ClCCl>[ClH:26].[C:23]([C:20]1[CH:21]=[C:22]2[C:17]([CH2:16][C:15](=[O:25])[N:14]2[CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:18][CH:19]=1)#[N:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59444141N-Boc 4-(6-Cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine

Product 1

HCID 684835434-(6-cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-Boc 4-(6-cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine (D136, 400 mg, 1.172 mmol) in dichloromethane (5 mL) was treated with 4M HCl in dioxane (5 mL, 20.00 mmol). After 4 h at room temperature, evaporation and crystallisation from diethyl ether gave white crystals of 4-(6-cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine hydrochloride (270 mg, 0.972 mmol, 83% yield).

Workup

  1. customevaporation and crystallisation from diethyl ether

Sources & evidence

ORD record
ord-9c04f61109a3419ea5f96f7690521356
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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