tert-Butyl 4-(2-fluoroethyl)piperazine-1-carboxylate → 1-(2-Fluoroethyl)piperazine dihydrochloride

HRID 419362Notes

Reaction equation

HRID 419362 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1.[ClH:17].CO>CO>[ClH:17].[ClH:17].[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 21082715tert-Butyl 4-(2-fluoroethyl)piperazine-1-carboxylateHCID 21893726Hydrochloride methanol

Product 1

HCID 665456881-(2-Fluoroethyl)piperazine dihydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To the solution of 1,1-dimethylethyl 4-(2-fluoroethyl)-1-piperazinecarboxylate (from a different batch than previously described) (160 g, 0.68 mol) in MeOH (500 mL) was added HCl/MeOH (5M, 1000 mL), and the mixture was heated at 50° C. for 1 h before evaporating most of the solvent. The residue was filtered and washed with MeOH to give the title compound of Step B (122 g, 87% yield). 1H NMR (400 MHz, D2O) δ ppm 3.60-3.78 (m, 10H), 4.80 (t, J=4.4 Hz, 1H), 4.92 (t, J=4.4 Hz, 1H)

Workup

  1. custombefore evaporating most of the solvent
  2. filtrationThe residue was filtered
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-ea8fbbb23624483c9794fb671f130cf3
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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