1-Chloro-2-nitrobenzene → 4-[(2-Nitrophenoxy)methyl]piperidine

HRID 1389242Notes

Reaction equation

HRID 1389242 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].[OH-].[K+]>O1CCOCC1>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 14797Potassium HydroxideHCID 4207714-Piperidinemethanol

Product 1

HCID 202988744-[(2-Nitrophenoxy)methyl]piperidineYield 22.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 23.0 g (0.2 mole) of 4-hydroxymethylpiperidine, 31.5 g (0.2 mole) of 2-chloronitrobenzene, 11.8 g (0.21 mole) of potassium hydroxide and 200 ml of dioxane is heated to 70° C. for 3 days. The reaction mixture is then evaporated in a vacuum and the residue is taken up in diethyl ether, washed with water, extracted with dilute hydrochloric acid, rendered alkaline and the aqueous mixture extracted with diethyl ether. After evaporation of the solvent, there are obtained 10.5 g of 4-(2-nitrophenoxymethyl)-piperidine (22% of theory); b.p. 130°-132° C./0.01 mm. Hg.

Workup

  1. customThe reaction mixture is then evaporated in a vacuum
  2. washwashed with water
  3. extractionextracted with dilute hydrochloric acid
  4. extractionthe aqueous mixture extracted with diethyl ether
  5. customAfter evaporation of the solvent, there

Sources & evidence

ORD record
ord-7c95348764444583b21e444d0cd92f7c
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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