1,1-Dichloroethane → 1-(3-Chloropyridin-2-yl)piperazine

HRID 1868010Notes

Reaction equation

HRID 1868010 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O.ClC(Cl)C>ClCCl>[Cl:1][C:2]1[C:3]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 6422Trifluoroacetic acid2×HCID 11630777Tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 114129441-(3-Chloropyridin-2-yl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a clear solution of tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate in anhydrous dichloromethane (25 mL) was added TFA (25 mL) dropwise. The yellow solution was stirred at room temperature for 2.5 hour. Reaction was complete as determined by TLC. TFA was azeotropped with dichloroethane to give 1-(3-chloropyridin-2-yl)piperazine in quantitative yield (1.265 g).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-30b29d4f567642f38fcd9d67ddf87c72
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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