Methyl Isocyanate → HCID 14649993, compound

HRID 1721856Notes

Reaction equation

HRID 1721856 reaction equation
[C:1]1([C:7]2([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][N:25]=[C:26]=[O:27]>C1C=CC=CC=1>[CH3:24][NH:25][C:26]([N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)[CH2:12][CH2:11]1)=[O:27]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 20029944HCID 20029944, compound

Product 1

HCID 14649993HCID 14649993, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.22 g of 4-phenyl-4-(3-trifluoromethylphenoxy)piperidine in 50 ml of benzene was added 0.40 g of methyl isocyanate. The reaction mixture was stirred at room temperature for 2.5 hours. Evaporation of the volatile afforded an oil which was purified by means of high pressure liquid chromatography (silica gel; elution with 50% ethyl acetate/dichloromethane) to yield 2.04 g (77%) of 1-(N-methylamino)carbonyl-4-phenyl-4-(3-trifluoromethylphenoxy)piperidine, m.p. 124°-127° C.

Workup

  1. customEvaporation of the
  2. customvolatile afforded an oil which
  3. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 50% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-5e0ed97b177b4e6697d909be748909c6
Source dataset
uspto-grants-1989_08
Patent number
US04853384

Reaction notes

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