4-Chlorophenyl Isocyanate → HCID 19887469, compound

HRID 654445Notes

Reaction equation

HRID 654445 reaction equation
[C:1]([C:4]1([OH:25])[CH2:9][CH2:8][N:7]([CH2:10][CH:11]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1.[H][H]>C(N(CCC)CCC)CC.C(OC(C)C)(C)C>[ClH:26].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:1]([OH:3])([CH3:2])[C:4]3([CH2:5][CH2:6][N:7]([CH2:10][CH:11]=[C:12]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:8][CH2:9]3)[O:25][C:34]2=[O:35])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 19887471HCID 19887471, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19887469HCID 19887469, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 7616TripropylamineSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A solution containing 6.4 g of 4-acetyl-1-(3,3-diphenyl-2-propenyl)-4-hydroxypiperidine and 3.4 g of 4-chlorophenyl isocyanate in 30 ml of tripropylamine is gently refluxed under argon while stirring for 3 hours, then the solvent is distilled off under reduced pressure. After adding benzene to the evaporation residue, the insoluble materials are filtered off, the benzene solution is filtered through a silica gel layer and the solution is evaporated under reduced pressure. After recrystallizing the crude product from a mixture of ethanol and hexane under clarifying with activated carbon, the base obtained is converted to its hydrochloride salt by adding a solution of hydrogen in diisopropyl ether. The title hydrochloride is obtained in 47.3% yield, m.p.: 227°-230° C. (with decomposition).

Workup

  1. temperatureis gently refluxed under argon
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionAfter adding benzene to the evaporation residue
  4. filtrationthe insoluble materials are filtered off
  5. filtrationthe benzene solution is filtered through a silica gel layer
  6. customthe solution is evaporated under reduced pressure
  7. customAfter recrystallizing the crude product
  8. additionfrom a mixture of ethanol and hexane
  9. customthe base obtained

Sources & evidence

ORD record
ord-e93a670e32154083917b33654e82d392
Source dataset
uspto-grants-1992_07
Patent number
US05132309

Reaction notes

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