Benzoyl chloride → (R)-1-Benzoyl-3-methylpiperazine

HRID 1689969Notes

Reaction equation

HRID 1689969 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.C(=O)(O)[O-].[Na+].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O.CC(C)=O>[CH3:1][C@H:2]1[NH:3][CH2:4][CH2:5][N:6]([C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:20])[CH2:7]1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 7578227(R)-1-Benzoyl-3-methylpiperazine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

(R)-2-methylpiperazine (13.85 g, 138 mmol), and sodium bicarbonate (52.3 g, 622 mmol) were dissolved/suspended in water (182 mL) and acetone (112 mL). The flask was cooled in an ice bath and a solution of benzoyl chloride (17.7 mL, 152 mmol) in acetone (56 mL) was added drop-wise over 1 hour. After 16 hours the acetone was removed on the rotovap. Water (400 mL) was added and the resulting mixture acidified using 6 M HCl to pH <2. The aqueous layer was washed with 200 mL CH2Cl2 three times. Aqueous sodium hydroxide (5M) was added to pH >12, and this solution was extracted three times with 200 mL of CH2Cl2. The combined organics were dried (MgSO4) and evaporated to give a thick yellow oil. MS (M+H)+=205.1

Workup

  1. temperatureThe flask was cooled in an ice bath
  2. customAfter 16 hours the acetone was removed on the rotovap
  3. additionWater (400 mL) was added
  4. washThe aqueous layer was washed with 200 mL CH2Cl2 three times
  5. additionAqueous sodium hydroxide (5M) was added to pH >12
  6. extractionthis solution was extracted three times with 200 mL of CH2Cl2
  7. dry with materialThe combined organics were dried (MgSO4)
  8. customevaporated
  9. customto give a thick yellow oil

Sources & evidence

ORD record
ord-ddb649697e8d41c0ba7f8e8f475b7824
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

Loading…