1,4-Dioxane hydrochloride → 4-Phenyl-1-pyrrolidin-3-yl-piperidine dihydrochloride

HRID 406468Notes

Reaction equation

HRID 406468 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH2:9]1)=O)(C)(C)C.[ClH:25].O1CCOCC1>>[ClH:25].[ClH:25].[C:19]1([CH:16]2[CH2:15][CH2:14][N:13]([CH:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)[CH2:18][CH2:17]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 597646213-(4-Phenyl-piperidin-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 688998884-Phenyl-1-pyrrolidin-3-yl-piperidine dihydrochlorideYield 61%

Procedure

A solution of 3-(4-phenyl-piperidin-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (preparation #5) (4.3 g, 13.1 mmol) in 4N HCl/dioxane (7 mL) was stirred at ambient temperature for about 16 h. The precipitate was collected by filtration, rinsed with Et2O (20 mL) and dried in vacuo to afford 4-phenyl-1-pyrrolidin-3-yl-piperidine dihydrochloride (2.4 g, 61%) as a hygroscopic beige solid that was used in subsequent reaction without further purification. RP-HPLC (Table 1, Method d) Rt 1.67 min; m/z: (M+H)+ 231.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washrinsed with Et2O (20 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-6621753e2ab246068358ae1756003645
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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