(Isocyanatomethylene)dibenzene → 1-Benzhydryl-3-(1-benzhydryl-pyrrolidin-3-ylmethyl)-urea

HRID 1295869Notes

Reaction equation

HRID 1295869 reaction equation
[CH:1]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][NH2:20])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH: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]([NH:20][CH2:19][CH:16]1[CH2:17][CH2:18][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:15]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 43344287C-(1-Benzhydryl-pyrrolidin-3-yl)-methylamine

Product 1

HCID 112944801-Benzhydryl-3-(1-benzhydryl-pyrrolidin-3-ylmethyl)-ureaYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of C-(1-benzhydryl-pyrrolidin-3-yl)-methylamine (0.26 g, 0.97 mmol) in dry CH2Cl2 (5 ml) was added diphenylmethyl isocyanate (0.18 ml, 0.97 mmol) drop wise under nitrogen. The resulting mixture was stirred at room temperature over night. Removal of solvent under reduced pressure followed by column chromatography using CH2Cl2: CH3OH (20:1) gives the desired product in 80% yield.

Workup

  1. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-629e418fbf5a43cc8ef64edfb8efe243
Source dataset
uspto-grants-2007_07
Patent number
US07244758B2

Reaction notes

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