Methyl Isocyanate → HCID 14649990, compound

HRID 1721855Notes

Reaction equation

HRID 1721855 reaction equation
[C:1]1([C:7]2([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][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:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)[CH2:12][CH2:11]1)=[O:27]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 212682524-Phenyl-4-(4-trifluoromethylphenoxy)piperidine

Product 1

HCID 14649990HCID 14649990, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 3.89 g of 4-phenyl-4-(4-trifluoromethylphenoxy)piperidine in 25 ml of benzene was added a solution of 0.68 g of methyl isocyanate in 25 ml of benzene. The reaction mixture was stirred for four hours at room temperaure. Evaporation of the volatiles afforded a solid which was purified by means of high pressure liquid chromatography (silica gel; elution with 50% ethyl acetate/dichloromethane). Recrystallization from 30% hexane/isopropyl ether yielded 2.46 g (54.19%) 1-(N-methylamino)carbonyl-4-phenyl-4-(4-trifluoromethylphenoxy)piperidine, m.p. 118°-120° C.

Workup

  1. customEvaporation 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)
  4. customRecrystallization from 30% hexane/isopropyl ether

Sources & evidence

ORD record
ord-2a729842724a4f539e32fe7c03a132b4
Source dataset
uspto-grants-1989_08
Patent number
US04853384

Reaction notes

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