(4-Aminophenoxy)benzene → 1-[4-(4-Dimethylaminopiperidin-1-yl)phenyl]-3-(4-phenoxyphenyl)urea

HRID 1354677Notes

Reaction equation

HRID 1354677 reaction equation
CN(C)C1CCNCC1.FC1C=CC([N+]([O-])=O)=CC=1.[H][H].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH:32]([N:35]([CH3:37])[CH3:36])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1.C1N=CN([C:43]([N:45]2C=N[CH:47]=[CH:46]2)=[O:44])C=1.[O:50]([C:57]1[CH:63]=CC(N)=[CH:59][CH:58]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>>[CH3:36][N:35]([CH3:37])[CH:32]1[CH2:31][CH2:30][N:29]([C:26]2[CH:27]=[CH:28][C:23]([NH:22][C:43]([NH:45][C:46]3[CH:47]=[CH:63][C:57]([O:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[CH:58][CH:59]=3)=[O:44])=[CH:24][CH:25]=2)[CH2:34][CH2:33]1

Participants

7

Reactant 6

HCID 8764(4-Aminophenoxy)benzeneHCID 9590p-FluoronitrobenzeneHCID 682631,1'-CarbonyldiimidazoleHCID 417391N,N-Dimethylpiperidin-4-amineHCID 108894141-(4-aminophenyl)-N,N-dimethylpiperidin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 103204921-[4-(4-Dimethylaminopiperidin-1-yl)phenyl]-3-(4-phenoxyphenyl)urea

Procedure

Dimethylpiperidin-4-ylamine was reacted with 4-fluoronitrobenzene, the resulting nitro compound was reduced with hydrogen and finally the aniline ([1-(4-aminophenyl)piperidin-4-yl]dimethylamine) was reacted with CDI and 4-phenoxyaniline by method A, B and C. This resulted in the product with the molecular weight of 430.55 (C26H30N4O2); MS (ESI): 431 (M+H+).

Workup

  1. customThis resulted in the product with the molecular weight of 430.55 (C26H30N4O2)

Sources & evidence

ORD record
ord-ea27a03d8e4a4069a5739c371e59cd10
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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