Aluminium lithium hydride → HCID 178511315, compound

HRID 744564Notes

Reaction equation

HRID 744564 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]#[N:19])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][NH2:19])[CH2:15][CH2:16]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178511314HCID 178511314, compound

Product 1

HCID 178511315HCID 178511315, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(6-fluoro-1H-indazol-3-yl)-1-piperidinyl]-acetonitrile (6.1 g, 23.6 mmol) in dry THF (235 ml) was added (dropwise) lithium aluminum hydride (LAH) (28.4 mmol, 1.0M in THF) at room temperature, under nitrogen. Upon complete addition, the reaction mixture was warmed to reflux for 3 hours. After cooling to 0 C in an ice bath, the reaction was carefully quenched with water (4.0 ml). The solids were removed via filtration and washed with THF. The combined filtrates were concentrated to give 5.6 g of the desired product. This material was suspended in DCM and filtered to give the product as an off-white solid, m.p. 125°-128° C.

Workup

  1. additionUpon complete addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux for 3 hours
  4. temperatureAfter cooling to 0 C in an ice bath
  5. customthe reaction was carefully quenched with water (4.0 ml)
  6. customThe solids were removed via filtration
  7. washwashed with THF
  8. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-689de23fc796489f9b1422b13e1784d9
Source dataset
uspto-grants-1996_09
Patent number
US05559126

Reaction notes

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