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

HRID 737136Notes

Reaction equation

HRID 737136 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>[C:31]1([NH:32][C:33]([N:13]2[CH2:12][CH2:11][N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:30])([F:28])[F:29])=[CH:17][CH:16]=3)[CH2:9][CH:8]2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:34])[CH:9]=[CH:8][CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 690563552-Benzyl-4-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine-1-carboxylic acid phenylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above compound was made in the following manner: 100 mg of 3-benzyl-1-(2′-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine dissolved in dichloromethane, 1.1 equiv. methylisocyanate 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 product was identified by ES MS(+) (m/z 530).

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

Sources & evidence

ORD record
ord-f719f980ad9a47b19ef9fb21916a775a
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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