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

HRID 1031569
Notes
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Reaction equation

HRID 1031569 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 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-a4122509dc2144c98e87dbc23c738736
Source dataset
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04954507

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes