Piperidine → HCID 23150307, compound

HRID 657650Notes

Reaction equation

HRID 657650 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)=[CH:14][CH:13]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C)C=O>[O:23]=[C:20]1[CH2:21][CH2:22][CH:17]([CH2:16][C:15]2[CH:24]=[CH:25][C:12]([O:11][CH2:10][CH2:9][CH2:8][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:13][CH:14]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 23150319HCID 23150319, compound

Product 1

HCID 23150307HCID 23150307, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of potassium carbonate (369 mg) in a solution of 4-[4-(3-chloropropoxy)benzyl]cyclohexanone (250 mg) and piperidine (264 μL) in N,N-dimethylformamide (6 mL) is heated for three hours at a temperature close to 80° C., then for two days at a temperature close to 50° C. Solvent is evaporated and the residue partioned between ethyl acetate (10 mL) and water (10 mL). The organic phase is separated by decantation, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated under reduced pressure and purified by column chromatography using a gradient dichloromethane/methanol/ammonia from 99/1/0.1 to 98/2/0.2 to give 270 mg of 1-{3-[4-(4-oxocyclohex-1-yl)methylphenoxy]propyl}piperidine.

Workup

  1. temperatureis heated for three hours at a temperature
  2. customclose to 80° C.
  3. customfor two days at a temperature close to 50° C
  4. customSolvent is evaporated
  5. customThe organic phase is separated by decantation
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-044688873b7f464d8e6d30ff9b356c06
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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