Trifluoroacetic acid → HCID 59252229, compound

HRID 604295Notes

Reaction equation

HRID 604295 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([Cl:20])=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:20][C:15]1[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593218363-(4-BOC-piperazino)-2-chloropyridine

Product 1

HCID 59252229HCID 59252229, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir 4-(2-chloro-pyridin-3-yl)-piperazine-1-carboxylic acid t-butyl ester (2.00 g, 6.72 mmol) in DCM (50 mL) at room temperature, then add trifluoroacetic acid (5 mL). Stir the reaction for 2 hr. and remove solvents in vacuo, then form the free base using SCX-2® chromatography washing with methanol then eluting with around 3 M ammonia in methanol. Concentrate in vacuo to give 1-(2-chloro-pyridin-3-yl)-piperazine as a brown oil (1.47 g, 110% yield). MS (m/z): 198 (M+1).

Workup

  1. customthe reaction for 2 hr
  2. customand remove solvents in vacuo
  3. customform the free base
  4. washwashing with methanol
  5. washthen eluting with around 3 M ammonia in methanol
  6. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-d53115fe79244f20a14584e559ad9bb3
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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