Diethyl Ether → HCID 22468741, compound

HRID 394982Notes

Reaction equation

HRID 394982 reaction equation
[Si]([O:8][CH2:9][C:10]1([CH2:23][CH2:24][CH:25]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=3)[N:30]=[CH:29][C:28]=2[Cl:39])[OH:26])[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]1)(C(C)(C)C)(C)C.C(OCC)C>Cl.O1CCOCC1>[ClH:39].[ClH:39].[Cl:39][C:28]1[CH:29]=[N:30][C:31]2[C:36]([C:27]=1[CH:25]([OH:26])[CH2:24][CH2:23][C:10]1([CH2:9][OH:8])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 22469184HCID 22469184, compound

Product 1

HCID 22468741HCID 22468741, compoundYield 328.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 1.5 g of tert-butyl 4-(tert-butyldimethylsilanyloxymethyl)-4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidine-1-carboxylate in 6.5 cm3 of 5N hydrochloric acid dissolved in dioxane and 30 cm3 of dioxane was stirred at a temperature in the region of 20° C. for 17 hours. 100 cm3 of diethyl ether were added to the reaction mixture. The precipitate formed was filtered off to give 1.24 g of {4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-hydroxypropyl]piperidin-4-yl}methanol dihydrochloride in the form of a pale yellow solid.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off

Sources & evidence

ORD record
ord-5d6567c3eadb4c89ae2d7f7b781c4f15
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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