Hydrochloric Acid → 1-(2-Fluoroethyl)-4-(4-piperidinyl)piperazine trihydrochloride

HRID 419364Notes

Reaction equation

HRID 419364 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1.[ClH:23]>CO>[ClH:23].[ClH:23].[ClH:23].[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594526881,1-Dimethylethyl 4-[4-(2-fluoroethyl)-1-piperazinyl]-1-piperidinecarboxylate

Product 1

HCID 866251901-(2-Fluoroethyl)-4-(4-piperidinyl)piperazine trihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl 4-[4-(2-fluoroethyl)-1-piperazinyl]-1-piperidinecarboxylate (28.95 g, 91.78 mmol) was dissolved in 76 mL of MeOH and 76 mL 37% HCl was added. Reaction was stirred for 3 h and then concentrated in vacuo and to give 1-(2-fluoroethyl)-4-(4-piperidinyl)piperazine trihydrochloride (˜29 g) which was then dissolved in DMSO (200 mL). K2CO3 (63 g, 459 mmol) was added followed by 4-fluoro-2-(methyloxy)-1-nitrobenzene (15.7 g, 91.8 mmol) and the reaction mixture was heated to 80° C. and allowed to stir overnight. The mixture was then poured into H2O and extracted with EtOAc (3×). The combined organics were dried with MgSO4, filtered, and concentrated in vacuo. The resulting solids were triturated with diethyl ether to give the title compound of step E (27.13 g, 81%). MS (M+H, ES+) 367.

Workup

  1. customReaction
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbe132d932b74d0b9cc012ac3c97032e
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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