4-Nitrophenol → 1-[3-(4-Nitrophenoxy)propyl]piperidine

HRID 495449Notes

Reaction equation

HRID 495449 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([O-:13])=[O:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.CCOC(C)=O>[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:2][CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

7

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 79625Piperidine, 1-(3-chloropropyl)-

Product 1

HCID 20579281-[3-(4-Nitrophenoxy)propyl]piperidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a three-neck flask with an overhead mechanical stirrer, a mixture of 1-(3-chloropropyl)-piperidine (49.8 g, 0.308 mol), 4-nitrophenol (42.8 g, 0.308 mol) and K2CO3 (212 g, 1.53 mol), in anhydrous DMF (200 mL) was heated to 94° C. and stirred for 18 h. The mixture was cooled to RT then diluted with 2 L water. The organics were taken up in EtOAc (2 L) and washed twice with 2N NaOH (500 mL) then brine (200 mL). The combined organics were dried over anhydrous MgSO4 then concentrated under reduced pressure to give 1-[3-(4-nitro-phenoxy)-propyl]-piperidine as a yellowish oil.

Workup

  1. washwashed twice with 2N NaOH (500 mL)
  2. dry with materialThe combined organics were dried over anhydrous MgSO4
  3. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-4bd0f96b7d594befaebf83a55e4816a7
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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