Ammonia → HCID 18933448, compound

HRID 1598375Notes

Reaction equation

HRID 1598375 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][NH:8][C:9](=O)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1.N>C1COCC1>[CH3:7][NH:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 18933418HCID 18933418, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18933448HCID 18933448, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (243 mg, 6.40 mmol) in THF (10 ml) was added dropwise under ice-cooling a solution of N-methyl-2-[1-(p-fluorobenzyl)-2-piperidyl]acetamide (1.13 g, 4.26 mmol) in THF (20 ml). The mixture was stirred for 20 minutes and then heated under reflux for 1.5 hours. To the reaction mixture was added dropwise under ice-cooling aqueous ammonia (20 ml) and the mixture was stirred at room temperature for 3 hours. Then, it was filtered with Celite and the aqueous layer was extracted with chloroform (50 ml×3). The combined organic layer was washed with saturated aqueous sodium chloride (20 ml), dried over potassium carbonate and the solvent was distilled off under reduced pressure to give crude 2-(2-methylaminoethyl)-1-(p-fluorobenzyl)piperidine (860 mg). Yield=76%. This compound was used for the subsequent reaction without purification.

Workup

  1. additionwas added dropwise under ice-
  2. temperatureheated
  3. temperatureunder reflux for 1.5 hours
  4. additionTo the reaction mixture was added dropwise under ice-
  5. stirringthe mixture was stirred at room temperature for 3 hours
  6. filtrationThen, it was filtered with Celite
  7. extractionthe aqueous layer was extracted with chloroform (50 ml×3)
  8. washThe combined organic layer was washed with saturated aqueous sodium chloride (20 ml)
  9. dry with materialdried over potassium carbonate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cecfa6ec5e2541c88929d643c7679ade
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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