Aluminium lithium hydride → (4-Benzyl-1-methylpiperazin-2-yl)methanol

HRID 1919155Notes

Reaction equation

HRID 1919155 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH:10]([C:21](OC)=[O:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH:10]([CH2:21][OH:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 49766299HCID 49766299, compound

Product 1

HCID 19777247(4-Benzyl-1-methylpiperazin-2-yl)methanolYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 336a (1 g, 2.99 mmol) in 100 mL of anhydrous tetrahydrofuran was slowly added lithium aluminum hydride (342 mg, 8.98 mmol) at 0° C. and the mixture was stirred for 30 min. Then, it was refluxed for 3 h and the reaction mixture was poured onto ice portionwise. The resulting mixture was filtered and the filtrate was evaporated in vacuo. After addition of 100 mL brine to the residue, it was extracted with methylene chloride (100 mL×3). The combined organic layer was dried over Na2SO4, filtered, and concentrated to afford 336b as yellow oil (0.60 g, 91%). MS: [M+H]+ 221.

Workup

  1. customat 0° C.
  2. temperatureThen, it was refluxed for 3 h
  3. additionthe reaction mixture was poured onto ice portionwise
  4. filtrationThe resulting mixture was filtered
  5. customthe filtrate was evaporated in vacuo
  6. additionAfter addition of 100 mL brine to the residue, it
  7. extractionwas extracted with methylene chloride (100 mL×3)
  8. dry with materialThe combined organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f08b3461871841f3b85b01effb84d1a6
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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