Water → HCID 66628219, compound

HRID 1961644Notes

Reaction equation

HRID 1961644 reaction equation
Cl.[F:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[C:17]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28]Br)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[I-].[Na+].O>C(#N)C>[C:20]([O:19][C:17](=[O:18])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][N:12]1[CH2:13][CH2:14][CH:9]([C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([F:2])=[CH:16][CH:15]=2)[CH2:10][CH2:11]1)([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 10868765tert-butyl N-(4-bromobutyl)carbamate

Product 1

HCID 66628219HCID 66628219, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

4-(4-fluorobenzoyl)piperidine hydrochloride (0.5 g, 2.01 mmol) is suspended in acetonitrile (5 mL), 4-(Boc-amino) Butyl Bromide was added (0.569 g, 2.01 mmol) and sodium iodide (0.461 g, 3.02 mmol) and the mixture was stirred at 80° C. overnight. Water was added and the aqueous phase was extracted with 30 mL dichloromethane. The combined organic phases were dried with magnesium sulfate, filtrated concentrated and purified with column chromatography on silica using dichloromethane/Methanol (95/0.5) to yield 0.830 g, (2.1 mmol, 100% yield) of the title compound as a brown solid. MS (m/e): 379.2 (M+H+).

Workup

  1. extractionthe aqueous phase was extracted with 30 mL dichloromethane
  2. dry with materialThe combined organic phases were dried with magnesium sulfate
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. custompurified with column chromatography on silica

Sources & evidence

ORD record
ord-20a0be04ebec4dc3b790c4c452acecbc
Source dataset
uspto-grants-2013_04
Patent number
US08415350B2

Reaction notes

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