3-Iodo-p-toluidine → 1-[4-(3-Iodo-4-methyl-phenylcarbamoyl)-phenyl]-piperidine-4-carboxylic acid ethyl ester

HRID 2190568Notes

Reaction equation

HRID 2190568 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[CH2:10]([O:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=[O:14])[CH3:11].C(OC(C1CCN(C2C=CC(C(=O)NC3C=CC=C(C(C)(C)C)C=3)=CC=2)CC1)=O)C>CCOCC>[CH2:10]([O:12][C:13]([CH:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27](=[O:28])[NH:5][C:4]3[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([I:1])[CH:3]=3)=[CH:25][CH:26]=2)[CH2:19][CH2:20]1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 1188893-Iodo-p-toluidineHCID 190638644-[4-(Ethoxycarbonyl)piperidin-1-YL]benzoic acidHCID 593180531-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 593179891-[4-(3-Iodo-4-methyl-phenylcarbamoyl)-phenyl]-piperidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-[4-(3-Iodo-4-methyl-phenylcarbamoyl)-phenyl]-piperidine-4-carboxylic acid ethyl ester was prepared from 3-iodo-4-methyl aniline and 1-(4-carboxy-phenyl)-piperidine-4-carboxylic acid ethyl ester following a procedure similar to the one described in the synthesis of 1-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperidine-4-carboxylic acid ethyl ester above. The product was isolated after a silica gel column with a 20-50% Et2O in hexanes gradient followed by a 50% EtOAc in hexanes elution. HRMS m/z calcd for C22H25N2O3I [M+H]+: 493.0983. Found: 493.0982.

Workup

  1. washfollowed by a 50% EtOAc in hexanes elution

Sources & evidence

ORD record
ord-58d942c1cc1b43cca756ea7a22aefb55
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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