Potassium Iodide → N,N-diphenyl-4-[3-methylphenyl]-1-piperidinepropanamine butenedioate

HRID 1902676Notes

Reaction equation

HRID 1902676 reaction equation
C1(N(CCCCl)C2C=CC=CC=2)C=CC=CC=1.Cl.CC1C=C(C2CCNCC2)C=CC=1.[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+].[C:40]([OH:47])(=[O:46])[CH2:41][CH2:42][C:43]([OH:45])=[O:44].[C:48]1([N:54]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:55][CH2:56][CH2:57][N:58]2[CH2:63][CH2:62][CH:61]([C:64]3[CH:69]=[CH:68][CH:67]=[C:66]([CH3:70])[CH:65]=3)[CH2:60][CH2:59]2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(O)CCC>[C:40]([OH:47])(=[O:46])[CH:41]=[CH:42][C:43]([OH:45])=[O:44].[C:48]1([N:54]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:55][CH2:56][CH2:57][N:58]2[CH2:59][CH2:60][CH:61]([C:64]3[CH:69]=[CH:68][CH:67]=[C:66]([CH3:70])[CH:65]=3)[CH2:62][CH2:63]2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 106580533-(N,N-diphenylamino)-1-chloropropaneHCID 219369674-(3-Methylphenyl)piperidine--hydrogen chloride (1/1)HCID 86738711N,N-diphenyl-4-[3-methylphenyl]-1-piperidinepropanamine butanedioate

Product 1

HCID 70530333N,N-diphenyl-4-[3-methylphenyl]-1-piperidinepropanamine butenedioate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 7.37 g. (0.030 moles) of 3-[N,N-diphenylamino]-1-chloropropane, 6.0 g. (0.024 moles) of 4-(3-methylphenyl)-piperidine hydrochloride, 3.92 g. (0.024 moles) of potassium iodide, and 5.30 g. (0.050 moles) of sodium carbonate in 60 ml. of n-butanol is refluxed for about 16 hours. Solvent is evaporated and the residue is dissolved in chloroform and washed with water. The chloroform solution is dried and passed through a column of silica gel. The product is eluted with acetonitrile. The product fractions are combined, concentrated, and converted to the maleate salt in ether. The resulting crystals recrystallized from acetonitrile to give 7.2 g. of N,N-diphenyl-4-[3-methylphenyl]-1-piperidinepropanamine butanedioate (1:1), mp. 137.5°-139.5° C.

Workup

  1. additionA mixture of 7.37 g
  2. customSolvent is evaporated
  3. dissolutionthe residue is dissolved in chloroform
  4. washwashed with water
  5. dry with materialThe chloroform solution is dried
  6. washThe product is eluted with acetonitrile
  7. concentrationconcentrated
  8. customThe resulting crystals recrystallized from acetonitrile
  9. customto give 7.2 g

Sources & evidence

ORD record
ord-e51816231e014e4ea3646c46d7142062
Source dataset
uspto-grants-1982_12
Patent number
US04364954

Reaction notes

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