HCID 12298008, compound → HCID 12298010, compound

HRID 1448327Notes

Reaction equation

HRID 1448327 reaction equation
[ClH:1].[C:2]1([N:8]([C:13]2([CH2:27][O:28]CC3C=CC=CC=3)[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[C:9](=[O:12])[CH2:10][CH3:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[ClH:1].[OH:28][CH2:27][C:13]1([N:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9](=[O:12])[CH2:10][CH3:11])[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 12298008HCID 12298008, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12298010HCID 12298010, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5.9 parts of N-phenyl-N-[1-(2-phenylethyl)-4-(phenylmethoxymethyl)-4-piperidinyl]propanamide hydrochloride and 120 parts of methanol is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and washed on the filter with methanol. The filtrate is evaporated. The oily residue solidifies on scratching. The solid product is crystallized from 20 parts of 2-propanone at room temperature. It is filtered off and recrystallized from 2-propanol at 0° C., yielding N-[4-(hydroxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide hydrochloride; mp. 218.4° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. washwashed on the
  3. filtrationfilter with methanol
  4. customThe filtrate is evaporated
  5. customThe solid product is crystallized from 20 parts of 2-propanone at room temperature
  6. filtrationIt is filtered off
  7. customrecrystallized from 2-propanol at 0° C.

Sources & evidence

ORD record
ord-435e227f1d954f5e91648d4b895f795a
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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