Phenylacetyl chloride → HCID 23339081, compound

HRID 26762Notes

Reaction equation

HRID 26762 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].[C:23]1([CH2:29][C:30]([Cl:32])=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1C=CC=CC=1>[ClH:32].[CH3:3][CH:2]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:30](=[O:31])[CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:6][CH2:5]1)[CH3:1]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 10340Sodium CarbonateHCID 23338998HCID 23338998, compound

Product 1

HCID 23339081HCID 23339081, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

to a stirred mixture of 4.4 parts of 1-(1-methylethyl)-N-phenyl-4-piperidinamine, 5.3 parts of sodium carbonate and 180 parts of benzene are added dropwise 5 parts of benzeneacetyl chloride. Upon completion, stirring is continued overnight at reflux. The reaction mixture is cooled, washed successively with water, a sodium hydrogen carbonate solution and again with water, dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2,2'-oxybispropane and 2-propanol. The formed salt is filtered off and crystallized from a mixture of 2-propanol and 2,2'-oxybispropane, yielding 2.5 parts of N-[1-(1-methylethyl)-4-piperidinyl]N-phenylbenzeneacetamide hydrochloride; mp. 184.4° C.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture is cooled
  3. washwashed successively with water
  4. dry with materiala sodium hydrogen carbonate solution and again with water, dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe formed salt is filtered off
  8. customcrystallized from a mixture of 2-propanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-7594cc1a2c944919b65548d545d57187
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Reaction notes

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