Sodium Hydroxide → HCID 23081599, compound

HRID 856082Notes

Reaction equation

HRID 856082 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:27])([F:26])[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][NH:23][CH:24]=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH3:24][NH:23][CH2:22][CH2:21][N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([C:8]([F:27])([F:7])[F:26])=[CH:10][CH:11]=2)[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86604795HCID 86604795, compound

Product 1

HCID 23081599HCID 23081599, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (237 mg, 6.25 mmol) was suspended in THF (20 ml), which was stirred while cooling in an ice-bath. To which a solution of N-{2-[4-(4-trifluoromethylphenyl)piperazin-1-yl]ethyl}-formamide (942 mg, 3.13 mmol) prepared in Reference Example 155 in THF (10 ml) was added dropwise, and the mixture was stirred at room temperature for 2 hours and then heated under reflux for 2 hours. The reaction mixture was allowed to return to room temperature, to which water and a 15% sodium hydroxide aqueous solution were added carefully. To the mixture, sodium sulfate was added, and the resulting mixture was vigorously stirred and filtered through Celite. The filtrate was concentrated under reduced pressure to afford N-methyl-{2-[4-(4-trifluoromethylphenyl)piperazin-1-yl]ethyl}-amine (900 mg, yield 100%) as a yellow oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. additionwas added dropwise
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. stirringthe resulting mixture was vigorously stirred
  7. filtrationfiltered through Celite
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6cffa77d37254739b484458e772436cf
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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