Methyl Isocyanate → HCID 19771979, compound

HRID 1614628Notes

Reaction equation

HRID 1614628 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH3:23][N:24]=[C:25]=[O:26]>C(Cl)Cl>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:10]2[CH2:15][CH2:14][N:13]([C:25]([NH:24][CH3:23])=[O:26])[CH2:12][CH2:11]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 19771957N,alpha-bis(4-fluorophenyl)-4-piperidinemethanamine

Product 1

HCID 19771979HCID 19771979, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.91 g (6.25 mmol) of the N,α-bis(4-fluorophenyl)-4-piperidinemethanamine and 0.45 g (7.9 mmol) of methyl isocyanate in 300 mL of CH2Cl2 was stirred at room temperature overnight. The solvent was removed in vacuo, and the residue was subjected to flash column chromatography (silica gel, gradiently eluted with 1 to 4% CH3OH in CH2Cl2) to give 1.54 g (68.6%) of white solid, mp 86°-90° C.

Workup

  1. customThe solvent was removed in vacuo
  2. washgradiently eluted with 1 to 4% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-73088c31170a4abf97d202b04508740d
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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