Propionic Acid → 3-Hydroxy-1-methyl-4-phenyl-4-propionoxy-piperidine

HRID 895045Notes

Reaction equation

HRID 895045 reaction equation
[O:1]1[C:7]2([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:2]1[CH2:3][N:4]([CH3:14])[CH2:5][CH2:6]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:27]([OH:31])(=[O:30])[CH2:28][CH3:29]>>[OH:1][CH:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([O:30][C:27](=[O:31])[CH2:28][CH3:29])[CH2:6][CH2:5][N:4]([CH3:14])[CH2:3]1

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 4350913-Methyl-6-phenyl-7-oxa-3-azabicyclo[4.1.0]heptaneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 129292363-Hydroxy-1-methyl-4-phenyl-4-propionoxy-piperidine

Procedure

A solution of 4.0 g of 3,4-epoxy-1-methyl-4-phenyl-piperidine and 4.5 g of p-toluenesulfonic acid monohydrate in 50 ml of propionic acid was stirred at room temperature for 10 minutes then the mixture evaporated to dryness. Water was added to the residue and the mixture made alkaline with sodium carbonate. The residual solid was filtered off and washed with water. Recrystallization of this solid from hot ethyl acetate gave 2.4 g of 3-hydroxy-1-methyl-4-phenyl-4-propionoxy-piperidine with a melting point of 142°-3° C. The corresponding hydrochloride salt had a melting point of 186°-8° C.

Workup

  1. customthe mixture evaporated to dryness
  2. additionWater was added to the residue
  3. filtrationThe residual solid was filtered off
  4. washwashed with water
  5. customRecrystallization of this solid from hot ethyl acetate

Sources & evidence

ORD record
ord-f986a5bab4664e3f895956f6f0368c26
Source dataset
uspto-grants-1981_08
Patent number
US04286095

Reaction notes

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