Trifluoroacetic acid → Ethyl 3-[2-(1-isopropylcarbamoyl-piperidin-4-yl)-ethoxy]-benzoate

HRID 1401138Notes

Reaction equation

HRID 1401138 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.[CH:37]([N:40]=[C:41]=[O:42])([CH3:39])[CH3:38]>C(Cl)Cl>[CH:37]([NH:40][C:41]([N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:5][CH2:6]1)=[O:42])([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 56830235Ethyl 3-(2-piperidin-4-yl-ethoxy)-benzoate

Product 1

HCID 66929612Ethyl 3-[2-(1-isopropylcarbamoyl-piperidin-4-yl)-ethoxy]-benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Ethyl 3-(2-piperidin-4-yl-ethoxy)-benzoate (1.0 g of the TFA salt, 2.6 mmol) was dissolved in DCM (10 ml), wereupon DIPEA (1.3 ml, 7.7 mmol) and isopropyl isocyanate (0.33 g, 3.8 mmol) was added. The reaction mixture was shaken overnight at 20° C. Silica gel (10 ml) was added, and the solvent removed in vacuo. Flash chromatography (EtOAc/heptan 35:65→55:45) provided 0.67 g of the title compound. LC-MS (m/z): 364 (M+2).

Workup

  1. additionSilica gel (10 ml) was added
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1361e4f6fc1b4a369e974b419c3c6176
Source dataset
uspto-grants-2014_12
Patent number
US08907096B2

Reaction notes

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