3-Iodo-p-toluidine → 4-[4-(3-Iodo-4-methyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2190643Notes

Reaction equation

HRID 2190643 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(OC(N1CCN(C2C=CC(C(=O)NC3C=CC=C(C(C)(C)C)C=3)=CC=2)CC1)=O)(C)(C)C>>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:24]=[CH:25][C:26]([C:29](=[O:30])[NH:5][C:4]3[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([I:1])[CH:3]=3)=[CH:27][CH:28]=2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 3

HCID 1188893-Iodo-p-toluidineHCID 27955084-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acidHCID 593180174-[4-(3-Tert-butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 593179654-[4-(3-Iodo-4-methyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Procedure

4-[4-(3-Iodo-4-methyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester was prepared from 3-iodo-4-methyl aniline and 4-(4-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester in a manner similar to the one described in the synthesis of 4-[4-(3-tert-butyl-phenylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester, above. The product was isolated after a silica gel purification with 10-30% Et2O in toluene. HRMS m/z calcd for C23H28N3O3I [M+H]: 522.1248. Found: 522.1246.

Workup

  1. customThe product was isolated
  2. customafter a silica gel purification with 10-30% Et2O in toluene

Sources & evidence

ORD record
ord-8cdaa6ae6df7477fb1c8c5709596b632
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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