Methyl Isocyanate → 1-(N-methylamino)carbonyl-4-(4-nitrophenoxy)-4-phenylpiperidine

HRID 1721853Notes

Reaction equation

HRID 1721853 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:23][N:24]=[C:25]=[O:26]>C1C=CC=CC=1>[CH3:23][NH:24][C:25]([N:12]1[CH2:11][CH2:10][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:22][CH:21]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:14][CH2:13]1)=[O:26]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 200299564-(4-Nitrophenoxy)-4-phenylpiperidine

Product 1

HCID 146499881-(N-methylamino)carbonyl-4-(4-nitrophenoxy)-4-phenylpiperidineYield 106.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 4.9 g of 4-(4-nitrophenoxy)-4-phenylpiperidine in 50 ml of benzene was added, dropwise, a solution of 0.91 g of methyl isocyanate in 15 ml of benzene. The reaction mixture was stirred at room temperature for two hours. 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) to yield 6.05 g of 1-(N-methylamino)carbonyl-4-(4-nitrophenoxy)-4-phenylpiperidine, m.p. 110°-115° 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)

Sources & evidence

ORD record
ord-53f75f66f3fe4404b46c4ba40058de92
Source dataset
uspto-grants-1989_08
Patent number
US04853384

Reaction notes

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