Methyl Isocyanate → HCID 57849618, compound

HRID 737116Notes

Reaction equation

HRID 737116 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]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])=[CH:16][CH:15]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:30][N:31]=[C:32]=[O:33]>C1COCC1>[CH3:30][NH:31][C:32]([N:12]1[CH2:11][CH2:10][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:28])([F:29])[F:27])=[CH:16][CH:15]=2)[CH2:8][CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:33]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 57849459HCID 57849459, compound

Product 1

HCID 57849618HCID 57849618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was made in the following manner: 55 mg of 3-phenyl-1-(2′-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine was dissolved in THF, 2 equiv. methylisocyanate were added. The reaction was shaken at room temperature overnight. The solvent was removed in vacuo, the residue was dissolved in 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 33 mg of the title compound as hydrochloride salt. Yield 48% ES MS m/z 454

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 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-83e94122fddd47a59bb197da44f63919
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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