4-Chlorophenyl Isocyanate → HCID 19887365, compound

HRID 654453Notes

Reaction equation

HRID 654453 reaction equation
[C:1]([C:4]1([OH:28])[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH:12]=[C:13]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1>C(N(CCC)CCC)CC>[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:12][CH2:11][CH2:10][N:7]2[CH2:6][CH2:5][C:4]3([O:28][C:37](=[O:38])[N:36]([C:33]4[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=4)[C:1]3=[CH2:2])[CH2:9][CH2:8]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 19887360HCID 19887360, compound

Product 1

HCID 19887365HCID 19887365, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 7616TripropylamineSolvent

Procedure

A solution containing 5.8 g of 4-acetyl-1-[4,4-bis(4-fluorophenyl)-3-butenyl]-4-hydroxypiperidine and 7.0 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 residue and filtering off the insoluble part, the benzene filtrate is filtered through a silica gel bed and evaporated under reduced pressure. The solid evaporation residue is recrystallized from ethanol under clarifying by activated carbon to obtain the title compound in 52% yield, m.p.: 186°-188° C.

Workup

  1. temperatureis gently refluxed under argon
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionAfter adding benzene to the residue
  4. filtrationfiltering off the insoluble part
  5. filtrationthe benzene filtrate is filtered through a silica gel bed
  6. customevaporated under reduced pressure
  7. customThe solid evaporation residue
  8. customis recrystallized from ethanol under clarifying by activated carbon

Sources & evidence

ORD record
ord-f8689cef60304f3e809c25ca62106b0a
Source dataset
uspto-grants-1992_07
Patent number
US05132303

Reaction notes

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