Hydrochloric Acid → (S)-1-Benzyl-3-methylpiperazine

HRID 1596215Notes

Reaction equation

HRID 1596215 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH3:21])=O)(C)(C)C.Cl>CO>[CH2:14]([N:11]1[CH2:12][CH2:13][NH:8][C@@H:9]([CH3:21])[CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10424333(S)-1-tert-butoxycarbonyl-2-methyl-4-benzylpiperazine

Product 1

HCID 6923224(S)-1-Benzyl-3-methylpiperazineYield 103.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of (S)-1-tert-butoxycarbonyl-2-methyl-4-benzylpiperazine (864 mg) in methanol (5 ml) was added concentrated hydrochloric acid (0.94 ml). The reaction mixture was stirred at 50° C. for 1 hour. After cooling, the solvent was evaporated off. The residue was made to alkali with 1N aqueous solution of sodium hydroxide and extracted with ethyl acetate (×3). The combined organic layer was dried over magnesium sulfate and concentrated to give (S)-1-benzyl-3-methylpiperazine (588 mg).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated off
  3. extractionextracted with ethyl acetate (×3)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f3cb0568baf14f7bbeda217f9e0046e5
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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