(Isocyanatomethylene)dibenzene → HCID 11591145, compound

HRID 2224134Notes

Reaction equation

HRID 2224134 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:21]1([CH:27]([N:34]=[C:35]=[O:36])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH:27]([NH:34][C:35]([N:18]1[CH2:19][CH2:20][N:15]([CH2:14][C:5]2([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH2:16][CH2:17]1)=[O:36])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 4250935(Isocyanatomethylene)dibenzeneHCID 68626046HCID 68626046, compound

Product 1

HCID 11591145HCID 11591145, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-((methyl-4-phenylpiperidin-4-yl)methyl)piperazine (0.135 g, 0.5 mmol) dissolved in methylene chloride (5 ml) was added diphenylmethyl isocyanate (0.115 g, 0.55 mmol) and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated. The residue was applied to flash column chromatography using methylene chloride and methanol (100:10) as eluents to give 0.13 g of desired product.

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-142e6cfbb08149e1a4a2614e1dc87ebb
Source dataset
uspto-grants-2008_05
Patent number
US07378420B2

Reaction notes

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