Trifluoroacetic acid → HCID 57807329, compound

HRID 2106517Notes

Reaction equation

HRID 2106517 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([N:24]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]2)[CH2:20][CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[N:24]1([CH:21]2[CH2:22][CH2:23][N:18]([C:16]([O:15][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:17])[CH2:19][CH2:20]2)[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54373813HCID 54373813, compound

Product 1

HCID 57807329HCID 57807329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 mL TFA were added at RT to 16.0 g (39.7 mmol) tert-butyl 4-(1-benzyloxycarbonyl-piperidin-4-yl)-piperazine-1-carboxylate in 200 mL DCM and the reaction mixture was stirred overnight at RT. It was evaporated down i. vac., the residue was taken up in 200 mL water and 200 mL EtOAc, the aqueous phase was separated off, combined with 50 mL 15% K2CO3 solution, extracted twice with 200 mL EtOAc and the combined organic phases were dried over Na2SO4. After elimination of the desiccant and solvent the residue was reacted with any further purification.

Workup

  1. customIt was evaporated down i
  2. custom200 mL EtOAc, the aqueous phase was separated off
  3. extractionextracted twice with 200 mL EtOAc
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. customAfter elimination of the desiccant and solvent the residue was reacted with any further purification

Sources & evidence

ORD record
ord-4535f362fa584258afcf8d48ca614eb4
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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