Trifluoroacetic acid → HCID 21101955, compound

HRID 1353314Notes

Reaction equation

HRID 1353314 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=O)[CH2:5][C:6]([CH3:12])=[N:7]2.O=P(Cl)(Cl)Cl.C(OC([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[CH:5][C:6]([CH3:12])=[N:7]2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24813Phosphorus oxychlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 69514742HCID 69514742, compound

Product 1

HCID 21101955HCID 21101955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,5-Dichloro-2-methylquinoline, obtained by treating 5-chloro-2-methyl-4-quinolone with POCl3 (cf. De, D., Byers L. D., Krogstad, D. J. J. Heterocyclic Chem. 1997, 34, 315; 1H NMR (CDCl3), δ 2.68 (s, 3H), 7.41 (s, 1H), 7.55 (t, 1H), 7.59 (dd, 1H), 7.95 (dd, 1H)), (125 mg, 0.59 mmol) and 1-tert-butoxycarbonylpiperazine (559 mg, 3.0 mmol) are reacted according to method A. The Boc group is cleaved with trifluoroacetic acid (3 mL) in CH2Cl2 (5 mL) giving 0.18 g of the piperazine.

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-eb0657727e4645debca4c617ca908cb0
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

Loading…