Ammonium Hydroxide → Ethyl [4-(methoxymethyl)piperidin-4-yl]phenylcarbamate

HRID 1448346Notes

Reaction equation

HRID 1448346 reaction equation
[CH2:1]([O:3][C:4]([N:6]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:7]1([CH2:23][O:24][CH3:25])[CH2:12][CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9][CH2:8]1)=[O:5])[CH3:2].[OH-].[NH4+].[H][H]>[Pd].CO>[CH3:25][O:24][CH2:23][C:7]1([N:6]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:4](=[O:5])[O:3][CH2:1][CH3:2])[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 53960004HCID 53960004, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54010374Ethyl [4-(methoxymethyl)piperidin-4-yl]phenylcarbamateYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 14.2 parts of (phenylmethyl) 4-[(ethoxycarbonyl)phenylamino]-4-(methoxymethyl)-1-piperidinecarboxylate and 1.8 parts of ammonium hydroxide in 120 parts of methanol is hydrogenated at normal pressure and at room temperature with 4 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is dissolved in 75 parts of trichloromethane. The solution is washed twice with water, dried, filtered and evaporated, yielding 7.9 parts (81.4%) of ethyl [4-(methoxymethyl)-4-piperidinyl]phenylcarbamate as a residue.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in 75 parts of trichloromethane
  4. washThe solution is washed twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-75c4a71946b64003a2c3bd12be2dcc36
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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