Methyl Isocyanate → HCID 57849494, compound

HRID 737124Notes

Reaction equation

HRID 737124 reaction equation
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=4[Cl:27])=[CH:16][CH:15]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][N:29]=[C:30]=[O:31]>ClCCl>[C:28]1([NH:29][C:30]([N:12]2[CH2:11][CH2:10][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=4[Cl:27])=[CH:16][CH:15]=3)[CH2:8][CH:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:31])[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 57849464HCID 57849464, compound

Product 1

HCID 57849494HCID 57849494, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

55 mg of 3-phenyl-1-(2′-chloro-5′-methyl-biphenyl-4-ylmethyl)-piperazine were dissolved in dichloromethane, 2 equiv. methylisocyanate were added. The reaction was shaken at room temperature overnight. The reaction was concentrated in vacuo. The residue was diluted with DCM, washed with 1M aqueous sodium hydroxide solution, then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to afford the title compound as free base. Addition of 1 equiv. of 1M HCl in dioxane and concentratation in vacuo afforded the title compound as hydrochloride salt. Yield 33%, ES MS m/z 496.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionThe residue was diluted with DCM
  3. washwashed with 1M aqueous sodium hydroxide solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-73250acc80054a6fbd27896175f2d421
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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