Boron tribromide → HCID 67265725, compound

HRID 1686064Notes

Reaction equation

HRID 1686064 reaction equation
Cl.[Cl:2][C:3]1[CH:21]=[C:20]([O:22]C)[CH:19]=[C:18]([Cl:24])[C:4]=1[CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:7]1=[O:17].B(Br)(Br)Br>ClC(Cl)C.ClCCl>[Cl:2][C:3]1[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([Cl:24])[C:4]=1[CH2:5][C@@H:6]1[CH2:10][CH2:9][N:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:7]1=[O:17]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 67265776HCID 67265776, compound

Product 1

HCID 67265725HCID 67265725, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Cool a solution of 3-(2,6-dichloro-4-methoxy-benzyl)-1-piperidin-1-yl-pyrrolidin-2-one hydrochloride (0.27 g) in dichloroethane (10 mL) to −20° C. and add 1 M solution of boron tribromide in dichloromethane (2.5 mL). Stir the reaction at −20° C. for 1 hour and at room temperature 12 hours. Partition the mixture with dichloromethane (20 mL) and saturated sodium bicarbonate (15 mL). Separate the organic layer. After drying the organic layer over sodium sulfate, filter and concentrate under vacuum to afford 0.18 g (76%) of the title compound. MS (m/z): 343 (M+).

Workup

  1. customthe reaction at −20° C. for 1 hour
  2. customat room temperature
  3. custom12 hours
  4. customPartition the mixture with dichloromethane (20 mL) and saturated sodium bicarbonate (15 mL)
  5. customSeparate the organic layer
  6. dry with materialAfter drying the organic layer over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-9a28841d98d24bb98d54f275e25fea8b
Source dataset
uspto-grants-2012_04
Patent number
US08148534B2

Reaction notes

Loading…