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10-Camphorsulfonyl chloride → 7,7-Dimethyl-1-(4-o-tolyl-piperazine-1-sulfonylmethyl)-bicyclo[2.2.1]heptan-2-one

HRID 2293574
Notes
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Reaction equation

HRID 2293574 reaction equation
Cl.[C:2]1([CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH3:15][C:16]1([CH3:29])[C:20]2([CH2:24][S:25](Cl)(=[O:27])=[O:26])[C:21]([CH2:23][CH:17]1[CH2:18][CH2:19]2)=[O:22]>C(Cl)(Cl)Cl>[CH3:15][C:16]1([CH3:29])[CH:17]2[CH2:18][CH2:19][C:20]1([CH2:24][S:25]([N:11]1[CH2:10][CH2:9][N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:14])[CH2:13][CH2:12]1)(=[O:27])=[O:26])[C:21](=[O:22])[CH2:23]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 26579910-Camphorsulfonyl chlorideHCID 122278951-(o-Tolyl)piperazine Hydrochloride

Product 1

HCID 29902137,7-Dimethyl-1-(4-o-tolyl-piperazine-1-sulfonylmethyl)-bicyclo[2.2.1]heptan-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, 0° C. solution of 1-(o-tolyl) piperazine hydrochloride (50.0 g; 235 mmol) and TEA (83 mL; 590 mmol) in chloroform (1000 mL) was added (+)-10-camphorsulfonyl chloride (65.5 g; 260 mmol). The solution was stirred at 0° C. for 1 h and then at ambient temperature for 3 h. The solution was extracted with 5% aqueous HCl (2×500 mL), water (500 mL), and saturated aqueous NaHCO3 (2×500 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The resulting solid was recrystallized from methanol to give the title compound, mp 112°-114° C. (69 g; 75%).

Workup

  1. waitat ambient temperature for 3 h
  2. extractionThe solution was extracted with 5% aqueous HCl (2×500 mL), water (500 mL), and saturated aqueous NaHCO3 (2×500 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-ec19690e9c034f08aafe8659cd960c2d
Source dataset
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05686454

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes