Dichloromethane → Ethyl 2-(4-((3,5-bis(trifluoromethyl)benzamido)methyl)piperidin-1-yl)ethylcarbamate

HRID 508629Notes

Reaction equation

HRID 508629 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH2:6][CH2:5]1.C(Cl)Cl.Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C=O)C>[F:26][C:23]([F:24])([F:25])[C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=1)[C:12]([NH:11][CH2:10][CH:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][NH:1][C:32](=[O:33])[O:34][CH2:35][CH3:36])[CH2:9][CH2:8]1)=[O:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10928Ethyl chloroformateHCID 57993201N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 57993262Ethyl 2-(4-((3,5-bis(trifluoromethyl)benzamido)methyl)piperidin-1-yl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide (66 mg, 0.17 mmol) in a 2:1 mixture of CH2Cl2:DMF (3 mL) and TEA (69 μL, 0.50 mmol) was treated with ethyl chloroformate (27 mg, 0.25 mmol). The reaction mixture was allowed to stir overnight, then the solvent was removed in vacuo and the residue was purified by HiTOPs.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by HiTOPs

Sources & evidence

ORD record
ord-0e19efc073384fd2ad4ac43387fa56e9
Source dataset
uspto-grants-2015_08
Patent number
US09096522B2

Reaction notes

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