Aluminium lithium hydride → HCID 57748298, compound

HRID 906060Notes

Reaction equation

HRID 906060 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][NH2:14])=[CH:15][CH:16]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 674037884-(1-Methylpiperidin-4-yl)benzamide

Product 1

HCID 57748298HCID 57748298, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cold solution of 4-(1-methylpiperidin-4-yl)benzamide (190 mg, 0.87 mmol) in tetrahydrofuran (5 mL) was added 1.0M lithium aluminum hydride in tetrahydrofuran (1.79 mL, 1.79 mmol) and stirring continued overnight at room temperature. The reaction mixture was quenched by adding sodium sulfate decahydrate until gas evolution ceased. The suspension was filtered through Celite and the filter cake washed with a mixture of ethyl acetate and chloroform (2:1, 50 mL). The filtrate was concentrated to give 4-(1-methylpiperidin-4-yl)benzylamine (130 mg, 71%) as an oil. 1H NMR (400 MHz, CDCl3): 7.23 (dd, 4H), 3.86 (s, 3H), 2.98 (m, 2H), 2.49 (m, 1H), 2.11 (m, 2H), 1.83 (m, 4H).

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding sodium sulfate decahydrate until gas evolution
  3. filtrationThe suspension was filtered through Celite
  4. washthe filter cake washed with a mixture of ethyl acetate and chloroform (2:1, 50 mL)
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-57b5c9593d1646fb824971cc27b5b5a4
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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