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

HRID 519307Notes

Reaction equation

HRID 519307 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

Compound 111a (1 g, 2.99 mmol) was dissolved in 100 mL of anhydrous tetrahydrofuran and lithium aluminum hydride (342 mg, 8.98 mmol) was added carefully 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 portion-wise. It was then filtered and the filtrate was evaporated in vacuo. After addition of 100 mL brine, it was extracted with dichloromethane (100 mL×3). The combined organic layer was dried over Na2SO4, filtered and concentrated to afford 111b as yellow oil (0.6 g, yield 91%)

Workup

  1. temperatureThen, it was refluxed for 3 h
  2. additionthe reaction mixture was poured onto ice portion-wise
  3. filtrationIt was then filtered
  4. customthe filtrate was evaporated in vacuo
  5. additionAfter addition of 100 mL brine, it
  6. extractionwas extracted with dichloromethane (100 mL×3)
  7. dry with materialThe combined organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-40a0d2b4551c4b5d8497a945072b10fe
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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