Hydrochloric Acid → Ethyl 4-(3-(aminomethyl)-4-fluorobenzyl)piperazine-1-carboxylate

HRID 1169600Notes

Reaction equation

HRID 1169600 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]1)#[N:2].Cl>CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68765124Ethyl 4-(3-cyano-4-fluorobenzyl)piperazine-1-carboxylate

Product 1

HCID 24859219Ethyl 4-(3-(aminomethyl)-4-fluorobenzyl)piperazine-1-carboxylateYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Ethyl 4-(3-cyano-4-fluorobenzyl)piperazine-1-carboxylate (5.9 g, 20.3 mmol, 1.0 equiv.) was dissolved in MeOH (47 mL), to which was added 12 M HCl (2.0 mL, 24.3 mmol, 1.2 equiv) while stirring vigorously. A catalytic amount of palladium on carbon (Aldrich, wet, 10% w/w) was then added as a MeOH slurry. The reaction was placed in a Parr bomb under atmosphere of H2 (55 psi) for 1 hour at room temperature. The reaction mixture was filtered through Celite and concentrated under reduced pressure to provide 5 g of ethyl 4-(3-(aminomethyl)-4-fluorobenzyl)piperazine-1-carboxylate.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e52953c489fe4c17aa91b73c3e338858
Source dataset
uspto-grants-2010_11
Patent number
US07825120B2

Reaction notes

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