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Aluminium lithium hydride → [2-(4-Trifluoromethyl-phenyl)-pyridin-4-yl]methylamine

HRID 1479802
Notes
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Reaction equation

HRID 1479802 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[F:17][C:2]([F:1])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([CH2:15][NH2:16])[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 668323802-(4-(Trifluoromethyl)phenyl)isonicotinonitrile

Product 1

HCID 68758847[2-(4-Trifluoromethyl-phenyl)-pyridin-4-yl]methylamineYield 82.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

The nitrile 20A (3 g, 12 mmol) dissolved in 50 ml of diethyl ether was added dropwise to a mixture of LiAlH4 (912 mg, 2 equiv.) in diethyl ether (80 mL) and stirred at 0° C. Then, the mixture was stirred at room temperature overnight. The excess of LiAlH4 was destroyed by water addition at 0° C., the solid formed was filtered, washed with Et2O and the filtrate was dried over Na2SO4 and evaporated to dryness to obtain 2.5 g of the amine as a yellow oil. The amine was used for the following step without purification.

Workup

  1. stirringThen, the mixture was stirred at room temperature overnight
  2. customThe excess of LiAlH4 was destroyed by water addition at 0° C.
  3. customthe solid formed
  4. filtrationwas filtered
  5. washwashed with Et2O
  6. dry with materialthe filtrate was dried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-92535d541b794091b6d8cb18cb1ad7b2
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409864B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes