Methyl Isocyanate → 2-Benzyl-4-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine-1-carboxylic acid methylamide

HRID 737135Notes

Reaction equation

HRID 737135 reaction equation
[CH2:1]([CH:8]1[NH:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][N:32]=[C:33]=[O:34]>ClCCl>[CH3:31][NH:32][C:33]([N:13]1[CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:28])[F:29])=[CH:17][CH:16]=2)[CH2:9][CH:8]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:34]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 235851083-Benzyl-1-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine

Product 1

HCID 578495812-Benzyl-4-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine-1-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound could be made in the following manner: 100 mg of 3-benzyl-1-(2′-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine would be dissolved in dichloromethane, 1.1 equiv. methylisocyanate would be added. The reaction would be shaken at room temperature overnight. The reaction would be concentrated in vacuo. The residue would be diluted with DCM, washed with 1M aqueous sodium hydroxide solution, then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue would be 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 would afford the title compound as hydrochloride salt.

Workup

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

Sources & evidence

ORD record
ord-3a9a2acb0df54b3e9479a48e6cdb0809
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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