Hydrochloric Acid → 4-(4-Nitrophenoxy)piperidine hydrochloride

HRID 1656595Notes

Reaction equation

HRID 1656595 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=O)C.[ClH:20]>>[ClH:20].[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([O:10][CH:7]2[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]2)=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23366963HCID 23366963, compound

Product 1

HCID 225914014-(4-Nitrophenoxy)piperidine hydrochlorideYield 100%

Procedure

A mixture of N-acetyl-4-(4-nitrophenoxy)piperidine (1.6 g. 6.05 mmol) and 2N HCl (25 mL) was heated under reflux for 3 hours. The mixture was cooled and concentrated to give 1.5 g (100%) of 4-(4-nitrophenoxy)piperidine hydrochloride as an off-white solid; mp 216°-219° C.; 1H NMR (DMSO-d6): δ 9.05 (br s, 2H), 8.10 (d, 2H), 7.10 (d, 2H), 4.82 (m, 1H), 3.08 (m, 2H), 3.00 (m, 2H), 2.05 (m, 2H), 1.85 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b405902c7f8e47ffaf314b909da5927e
Source dataset
uspto-grants-1993_10
Patent number
US05254689

Reaction notes

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