Aluminium lithium hydride → HCID 60036800, compound

HRID 1964795Notes

Reaction equation

HRID 1964795 reaction equation
[NH2:1][CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:3]1[CH2:8][CH2:7][N:6]([C:9](OC(C)(C)C)=O)[CH2:5][CH2:4]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:9][N:6]1[CH2:7][CH2:8][CH:3]([CH:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH2:1])[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 49760122HCID 49760122, compound

Product 1

HCID 60036800HCID 60036800, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate XXXI, e.g. tert-butyl 4-[amino(phenyl)methyl]piperidine-1-carboxylate (1.0 g, 3.44 mmol) was dissolved in dry THF (50 mL). LiAlH4 (261 mg, 6.89 mmol) was added in portions. The reaction was heated under reflux overnight. As the reaction was completed, it was quenched with dropwise addition of water (5 mL), followed by NaOH 1N (5 mL) and H2O (5 mL). The suspension thus obtained was extracted with ethyl acetate, dried over MgSO4 and evaporated, affording the crude product. It was further purified by flash chromatography (DCM/MeOH 20:1 with 2% NH4OH) to give the tertiary amine XXXII, e.g., 1-(1-methylpiperidin-4-yl)-1-phenylmethanamine (444.6 mg, 63% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux overnight
  3. customit was quenched with dropwise addition of water (5 mL)
  4. customThe suspension thus obtained
  5. extractionwas extracted with ethyl acetate
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customaffording the crude product
  9. customIt was further purified by flash chromatography (DCM/MeOH 20:1 with 2% NH4OH)

Sources & evidence

ORD record
ord-7936ed07285443d6abdc2ac61c5d7388
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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