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Water → HCID 66696142, compound

HRID 69116
Notes
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Reaction equation

HRID 69116 reaction equation
[C:1]1([C@@H:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:22][O:23][CH2:24][CH2:25]Br.O>CN(C=O)C.C(OCC)(=O)C>[CH3:22][O:23][CH2:24][CH2:25][N:12]1[CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][C@@H:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 809722-Bromoethyl methyl ether2×HCID 7173868rel-tert-butyl (3R)-3-phenylpiperazine-1-carboxylate

Product 1

HCID 66696142HCID 66696142, compound

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 330 mg of tert-butyl (3S)-3-phenylpiperazine-1-carboxylate in 3.5 mL of DMF was added 75.4 mg of sodium hydride (including 40% mineral oil) under ice-cooling, followed by stirring for 30 minutes. To the mixture was added 0.27 mL of 2-bromoethyl methyl ether, followed by stirring at room temperature for 16 hours. To the mixture were added 75.4 mg of sodium hydride (including 40% mineral oil) and 0.6 mL of 2-bromoethyl methyl ether, followed by further stirring for 8 hours. The mixture was poured into a mixture of water and ethyl acetate, and the aqueous layer was separated. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 330 mg of tert-butyl (3S)-4-(2-methoxyethyl)-3-phenylpiperazine-1-carboxylate.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 16 hours
  3. stirringby further stirring for 8 hours
  4. customthe aqueous layer was separated
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-675fb810c858404ba863909b3ae8a4db
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822448B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes