HCID 10446014, compound → HCID 10106660, compound

HRID 2293753Notes

Reaction equation

HRID 2293753 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][C:6]1[C:7]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:19][C:2]([F:1])([F:18])[CH2:3][NH:5][C:6]1[C:7]([N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 10446014HCID 10446014, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10106660HCID 10106660, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[3-(2,2,2-Trifluoroacetamido)-2-pyridinyl]piperazine (PREPARATION 35), is dissolved in 5 ml of tetrahydrofuran and cooled to 0°. Then 4.84 ml of lithium aluminum hydride solution is added dropwise. After 10 min of stirring at 0°, the reaction is warmed to 20°-25° and stirred 45 min. The reaction is quenched at 0° with the dropwise addition of 0.4 ml of water, 0.6 ml of 10% aqueous sodium hydroxide, and 1 ml of water. The slurry is filtered through celite, washed with 20% methanol/chloroform and concentrated in vacuo to afford the title amine which is used without further purification, NMR (300 MHz, CDCl3) 7.82, 6.97-6.92, 4.86, 3.75, and 3.06-3.01 δ.

Workup

  1. temperaturecooled to 0°
  2. temperaturethe reaction is warmed to 20°-25°
  3. stirringstirred 45 min
  4. customThe reaction is quenched at 0° with the dropwise addition of 0.4 ml of water, 0.6 ml of 10% aqueous sodium hydroxide, and 1 ml of water
  5. filtrationThe slurry is filtered through celite
  6. washwashed with 20% methanol/chloroform
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a41368c75157472f9c1ec5f12b6721db
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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