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

HRID 2194635
Notes
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Reaction equation

HRID 2194635 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent

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-4b0d84bceb20428db29ce1c8a4f24a5b
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08334305B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes