2-Bromopropane → 1-Isopropyl-4-(4-nitrophenoxy)-4-phenylpiperidine

HRID 1156033Notes

Reaction equation

HRID 1156033 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH:29](Br)([CH3:31])[CH3:30]>CC(CC)=O>[CH:29]([N:12]1[CH2:11][CH2:10][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:22][CH:21]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:14][CH2:13]1)([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 200299564-(4-Nitrophenoxy)-4-phenylpiperidine

Product 1

HCID 205365891-Isopropyl-4-(4-nitrophenoxy)-4-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

6.0 g of 4-(4-nitrophenoxy)-4-phenylpiperidine, 2.8 g of potassium carbonate and 3.0 g of isopropyl bromide are boiled under reflux in 50 ml of ethyl methyl ketone for 24 hours. The solvent is evaporated off, the residue is taken up in 100 ml of water, and the aqueous mixture is extracted with 100 ml of diethyl ether. The organic phase is dried over sodium sulfate, filtered over active charcoal and concentrated. 5.2 g of the title compound remain as a viscous, pale yellow oil.

Workup

  1. customThe solvent is evaporated off
  2. extractionthe aqueous mixture is extracted with 100 ml of diethyl ether
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered over active charcoal
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba7e6a70b68340b9ae608a98f0c95554
Source dataset
uspto-grants-1982_06
Patent number
US04333942

Reaction notes

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