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

HRID 1042698Notes

Reaction equation

HRID 1042698 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.C(OCC)(=O)C>[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-necked flask fitted 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 potassium carbonate (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 room temperature, then diluted with 2 L water. The organics were taken up in ethyl acetate and washed twice with 2N sodium hydroxide and then brine. The combined organics were dried over magnesium sulfate then concentrated under reduced pressure to give the title compound as a yellowish oil.

Workup

  1. customIn a three-necked flask fitted with an overhead mechanical stirrer
  2. washwashed twice with 2N sodium hydroxide
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-52da004ae7ee4932be4af4a614801a3f
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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