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(Diethylamino)sulfur trifluoride → 1,4-Dibenzyl-2-(fluoromethyl)piperazine

HRID 1089211
Notes
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Reaction equation

HRID 1089211 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[CH2:11][CH:12]1[CH2:17][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>ClCCl>[F:7][CH2:11][CH:12]1[CH2:17][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanol

Product 1

HCID 144794991,4-Dibenzyl-2-(fluoromethyl)piperazineYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

To a solution of 0.6 g (3.7 mmol) of diethylamino-sulfur trifluoride in 5 ml dichloromethane cooled at -78° C. under nitrogen was added dropwise a solution of 1 g (3.4 mmol) of 2-hydroxymethyl-1,4-di-phenylmethyl piperazine in 5 ml dichloromethane. The temperature of the solution was allowed to warm to -50° C. in 30 mn then to 0° C. in 1 hr 30 min. The solution was stirred two more hours at room temperature and cooled back to +5° C. A few drops of aqueous saturated solution of sodium bicarbonate were added until basic pH. The organic layer was washed twice with water, dried over magnesium sulfate, the solvent removed to give 1.10 g of an oil which was purified by chromatography using dichloromethane/ethyl acetate (95:5) to afford 0.46 g (42%) of title compound.

Workup

  1. temperaturecooled back to +5° C
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed

Sources & evidence

ORD record
ord-642a750391cb4bb3962777ffc2763759
Source dataset
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04965273

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes