Lithium Chloride → 3-Hydroxylmethyl-benzoylpiperazine

HRID 992357Notes

Reaction equation

HRID 992357 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:17]=[CH:18][CH:19]=1)[C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])=O)C.[Cl-].[Li+].[BH4-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.CCO>[OH:3][CH2:4][C:6]1[CH:7]=[C:8]([CH:17]=[CH:18][CH:19]=1)[C:9]([N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1)=[O:10]

Participants

7

Reactant 4

HCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 543618603-Ethoxycarbonyl-benzoylpiperazine

Product 1

HCID 185197513-Hydroxylmethyl-benzoylpiperazine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-ethoxycarbonyl-benzoylpiperazine XLIX (200 mg, 0.76 mmol) in THF (5 ml), was added lithium chloride (36 mg, 0.84 mmol), NaBH4 (32 mg, 0.84 mmol) and EtOH (5 ml) sequentially. After stirring for 8 hours at room temperature, a saturated NaHCO3 solution was added and the aqueous phase was extracted with ethyl acetate (3×20 ml). The organic layers were combined, dried over MgSO4 and concentrated to give a crude mixture, which was used for the further reaction without purification.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (3×20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-858d69991262437685df9be6dd8a01e8
Source dataset
uspto-grants-2002_10
Patent number
US06469006B1

Reaction notes

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