Methyl Isocyanate → 1-(N-methylamino)carbonyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine

HRID 1721859Notes

Reaction equation

HRID 1721859 reaction equation
[F:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:3]=1[O:4][C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH3:25][N:26]=[C:27]=[O:28]>C1C=CC=CC=1>[CH3:25][NH:26][C:27]([N:8]1[CH2:7][CH2:6][C:5]([O:4][C:3]2[C:17]([F:24])=[C:18]([F:23])[C:19]([F:22])=[C:20]([F:21])[C:2]=2[F:1])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:10][CH2:9]1)=[O:28]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 146499784-(2,3,4,5,6-Pentafluorophenoxy)-4-phenylpiperidine

Product 1

HCID 146499801-(N-methylamino)carbonyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidineYield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 5.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine in 50 ml of benzene was treated with a solution of 0.9 g of methyl isocyanate in 20 ml of benzene over a period of ten minutes. The reaction mixture was then stirred at ambient temperature for two hours. Evaporate of the volatiles afforded a solid which was purified by means of high pressure liquid chromatography (silica gel; elution with 50% ethyl acetate/dichloromethane) to yield 4.0 g (69%) of 1-(N-methylamino)carbonyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine, m.p. 87°-89° C.

Workup

  1. customEvaporate of the volatiles
  2. customafforded a solid which
  3. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 50% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-32ba7944d52a49e9ace3e7b2cd5c9a43
Source dataset
uspto-grants-1989_08
Patent number
US04853384

Reaction notes

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