alpha-Naphthyl isocyanate → HCID 19887348, compound

HRID 654452Notes

Reaction equation

HRID 654452 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][C:15]([C:19]#[CH:20])([OH:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[C:28]1([N:38]=[C:39]=[O:40])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1.C([O-])(=O)C.[K+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][C:15]3([O:18][C:39](=[O:40])[N:38]([C:28]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH:31]=[CH:30][CH:29]=4)[C:19]3=[CH2:20])[CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 66589alpha-Naphthyl isocyanateHCID 517044Potassium AcetateHCID 9907239HCID 9907239, compound

Product 1

HCID 19887348HCID 19887348, compoundYield 76.5%

Procedure

A mixture containing 11.0 g of 1-[4,4-bis(4-fluorophenyl)-3-butenyl]-4-ethynyl-4-hydroxypiperidine, 6.0 g of 1-naphthyl isocyanate, 0.2 g of anhydrous potassium acetate and 36 ml of C-picoline is refluxed under nitrogen while stirring for 5 hours. After evaporating the solvent under reduced pressure, the residue is taken up in benzene, filtered through an aluminum oxide column and then evaporated under reduced pressure. The residue is recrystallized from methanol under clarifying by activated carbon to give the title product in 76.5% yield, m.p.: 99°-101° C.

Workup

  1. temperatureis refluxed under nitrogen
  2. customAfter evaporating the solvent under reduced pressure
  3. filtrationfiltered through an aluminum oxide column
  4. customevaporated under reduced pressure
  5. customThe residue is recrystallized from methanol under clarifying by activated carbon

Sources & evidence

ORD record
ord-0044d6c67ced4deeae8fa4f8df46719b
Source dataset
uspto-grants-1992_07
Patent number
US05132303

Reaction notes

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