Methyl 1,4-di-Boc-piperazine-2-acetate → 2-(1,4-Dimethylpiperazin-2-yl)ethanol

HRID 2262477Notes

Reaction equation

HRID 2262477 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][CH:9]1[CH2:21][C:22](OC)=[O:23])=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH:9]1[CH2:21][CH2:22][OH:23]

Participants

4

Reactant 2

HCID 4055116Methyl 1,4-di-Boc-piperazine-2-acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 587843272-(1,4-Dimethylpiperazin-2-yl)ethanolYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-methoxycarbonylmethylpiperazine-1,4-dicarboxylic acid di-tert-butyl ester (662 mg, 1.85 mmol) in anhydrous THF (10 mL) at 0° C. was slowly added a 1M solution of LiAlH4 in THF (5.7 mL, 5.70 mmol). The stirred reaction mixture was allowed to warm to room temperature over a period of 15 minutes before being refluxed for 2 hours. After this time the reaction mixture was cooled to 0° C. and cautiously quenched by the dropwise addition of 1.0M aqueous NaOH solution until the effervescing ceased. The resulting gel was diluted with THF (50 mL) and the solids filtered off. The filtrate was concentrated in vacuo to afford 2-(1,4-dimethylpiperazin-2-yl)ethanol (191 mg, 65%) as a colourless oil.

Workup

  1. customThe stirred reaction mixture
  2. temperaturebefore being refluxed for 2 hours
  3. temperatureAfter this time the reaction mixture was cooled to 0° C.
  4. customcautiously quenched by the dropwise addition of 1.0M aqueous NaOH solution until the effervescing
  5. additionThe resulting gel was diluted with THF (50 mL)
  6. filtrationthe solids filtered off
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-37549b1dde2c41e08ed6576ea572f25b
Source dataset
uspto-grants-2010_12
Patent number
US07851471B2

Reaction notes

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