Hydrochloric Acid → 4-(2H-1,3-Benzodioxol-5-yl)piperidin-4-ol

HRID 1576665Notes

Reaction equation

HRID 1576665 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([OH:23])([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>[Pd].CO>[OH:23][C:11]1([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 221280344-(2H-1,3-Benzodioxol-5-yl)-1-benzylpiperidin-4-ol

Product 1

HCID 150347154-(2H-1,3-Benzodioxol-5-yl)piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

39.4 g. 1-benzyl-4-hydroxy-4-(3.4-methylene dioxy phenyl)-piperidine are dissolved in 400 ml. methanol and the solution is mixed with 30 ml. 4-N hydrochloric acid. To this mixture is then added 3 g. of a palladium/carbon catalyst which has been suspended in 60 ml. alcohol. The mixture is hydrogenized at 35° - 40°C under normal pressure. After 3300 ml. hydrogen has been absorbed, hydrogenation is stopped and the cataylst is removed from the mixture by filtering. The mother liquor is heavily concentrated and the 4-hydroxy-4-(3.4-methylene dioxy phenyl)-piperidine hydrochloride with a melting point of 198° - 200°C crystallizes out.

Workup

  1. additionTo this mixture is then added 3 g
  2. customis hydrogenized at 35° - 40°C under normal pressure
  3. customhydrogen has been absorbed
  4. customthe cataylst is removed from the mixture
  5. filtrationby filtering
  6. concentrationThe mother liquor is heavily concentrated
  7. customthe 4-hydroxy-4-(3.4-methylene dioxy phenyl)-piperidine hydrochloride with a melting point of 198° - 200°C crystallizes out

Sources & evidence

ORD record
ord-89166f60b9bf43cc8968d0cdaad1fb37
Source dataset
uspto-grants-1976_09
Patent number
US03982001

Reaction notes

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