Hydrochloric Acid → 4-(4-Chlorophenyl)-4-methoxypiperidine

HRID 1977302Notes

Reaction equation

HRID 1977302 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([O:14][CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O>C(OCC)(=O)C>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]2([O:14][CH3:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 219975781-Tert-butoxycarbonyl-4-(4-chlorophenyl)-4-methoxypiperidine

Product 1

HCID 224946584-(4-Chlorophenyl)-4-methoxypiperidineYield 78.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of 1-tert-butoxycarbonyl-4-(4-chlorophenyl)-4-methoxypiperidine (0.72 g) in ethyl acetate (10 ml) was added 4N HCl in ethyl acetate (5.5 ml). After stirring for 6.7 hours, the reaction mixture was poured into a mixture of ethyl acetate and water, followed by alkalification of the solution to pH 12. The organic layer was successively washed with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to give 4-(4-chlorophenyl)-4-methoxypiperidine (0.39 g).

Workup

  1. washThe organic layer was successively washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-30383cd92d85488a896b470693025177
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

Loading…