N-(4-Chlorophenyl)-1-isopropylpiperidin-4-amine → {4-[2-{(4-Chlorophenyl)[1-(1-methylethyl)-4-piperidinyl]amino}-2-oxoethyl]phenyl} ethyl carbonate

HRID 1704442

Reaction equation

HRID 1704442 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:17])[CH3:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:18](=[O:33])([O:30][CH2:31][CH3:32])[O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1>CC(C)CC(=O)C>[C:18](=[O:33])([O:30][CH2:31][CH3:32])[O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][C:27]([N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:17])[CH3:16])[CH2:11][CH2:10]2)=[O:28])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 3017394N-(4-Chlorophenyl)-1-isopropylpiperidin-4-amineHCID 203340744-(2-Chloro-2-oxoethyl)phenyl ethyl carbonate

Product 1

HCID 54328184{4-[2-{(4-Chlorophenyl)[1-(1-methylethyl)-4-piperidinyl]amino}-2-oxoethyl]phenyl} ethyl carbonate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a stirred mixture of 7.5 parts of N-(4-chlorophenyl)-1-(1-methylethyl)-4-piperidinamine and 80 parts of 4-methyl-2-pentanone are added dropwise 9 parts of [4-(2-chloro-2-oxoethyl)-phenyl] ethyl carbonate. Upon completion, the whole is heated to reflux and stirring is continued for one hour at reflux temperature. After cooling, the precipitated product is filtered off and stirred for 30 minutes in a mixture of alkaline water and trichloromethane. The layers are separated. The organic phase is dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated yielding 5.5 parts of {4-[2-{(4-chlorophenyl)-[1-(1-methylethyl)-4-piperidinyl]amino}-2-oxoethyl]phenyl} ethyl carbonate as an oily residue.

Workup

  1. temperatureUpon completion, the whole is heated
  2. temperatureto reflux
  3. temperatureat reflux temperature
  4. temperatureAfter cooling
  5. filtrationthe precipitated product is filtered off
  6. stirringstirred for 30 minutes in a mixture of alkaline water and trichloromethane
  7. customThe layers are separated
  8. customThe organic phase is dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe oily residue is purified by column-chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  13. customThe pure fractions are collected
  14. customthe eluent is evaporated

Sources & evidence

ORD record
ord-e5f1561514c34a1b84a422a3729ee3a3
Source dataset
uspto-grants-1978_11
Patent number
US04126689

Linked notes

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