Ethyl Acetate → HCID 15540529, compound

HRID 970401Notes

Reaction equation

HRID 970401 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.[OH-].[Na+].CCOC(C)=O>Cl.O1CCOCC1>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)[CH2:16][CH2:17]2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 54284239HCID 54284239, compound

Product 1

HCID 15540529HCID 15540529, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(+/−)-N-(t-butoxycarbonyl)-2-[[4-[(4-fluorophenyl)methyl]-1-piperidinyl]methyl]-piperidine (340 mg, 0.87 mmol) was dissolved in 4M HCl in dioxane (10 mL). The reaction was stirred for 1 h and then conc. in vacuo to a white solid. The solid was partioned between 10% NaOH and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, dried over MgSO4, and conc. in vacuo to a white solid yielding 250 mg of product. MS (ESI) 291 (M+H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-a8237d4925b94d98992f3bf73d15dc89
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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