Aluminium lithium hydride → 2-Amino-1-(1-benzylpiperidin-4-yl)ethan-1-ol

HRID 1787702Notes

Reaction equation

HRID 1787702 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH:8]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)[C:9]#[N:10]>C1COCC1>[NH2:10][CH2:9][CH:8]([CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:15][CH2:16]1)[OH:7]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57599582Hydroxy[1-(phenylmethyl)-4-piperidinyl]acetonitrile

Product 1

HCID 575995752-Amino-1-(1-benzylpiperidin-4-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LiAlH4 (1.1 g, 28.7 mmol) in THF (25 mL) at 0° C. was added dropwise via addition funnel a solution of hydroxy[1-(phenylmethyl)-4-piperidinyl]acetonitrile (2.2 g, 9.56 mmol) in THF (25 mL). After 12 h at 25° C., the solution was carefully quenched by dropwise additional of sodium potassium tartrate and extracted several times with DCM. The combined organic fractions were dried (Na2SO4) and concentrated yielding the title compound as a yellow oil which was used without further purification: LCMS (ES) m/e 235 (M+H)+.

Workup

  1. customthe solution was carefully quenched by dropwise additional of sodium potassium tartrate
  2. extractionextracted several times with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a1a82202107b4eb58f667246f28292f6
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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