Aluminium lithium hydride → HCID 18351405, compound

HRID 1787698Notes

Reaction equation

HRID 1787698 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1([CH2:21][C:22]([NH2:24])=O)[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1>C1COCC1>[NH2:24][CH2:22][CH2:21][C:8]1([OH:7])[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57599580HCID 57599580, compound

Product 1

HCID 18351405HCID 18351405, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of LiAlH4 (1.8 g, 0.048 mmol) in THF (40 mL) at 0° C. was added dropwise via addition funnel a solution of 2-[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]acetamide (4 g, 0.016 mmol) in THF (40 mL). The solution warmed to 25° C. and was then heated to reflux for 12 h. After cooling, the solution was then carefully quenched with a saturated solution of sodium potassium tartrate and extracted several times with DCM. The combined organic fractions were dried (Na2SO4) and the resulting residue was used directly without further purification: LCMS (ES) m/e 236 (M+H)+.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for 12 h
  3. temperatureAfter cooling
  4. customthe solution was then carefully quenched with a saturated solution of sodium potassium tartrate
  5. extractionextracted several times with DCM
  6. dry with materialThe combined organic fractions were dried (Na2SO4)
  7. customthe resulting residue was used directly without further purification

Sources & evidence

ORD record
ord-6d6298efaa5e43d792fd28026cd8487b
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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