Boron tribromide → 1-[5-Hydroxy-2-(4-pyridinylamino)benzoyl]piperidine

HRID 64888Notes

Reaction equation

HRID 64888 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:7]([CH:16]=1)[C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:7]([CH:16]=1)[C:8]([N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13712456HCID 13712456, compound

Product 1

HCID 137124571-[5-Hydroxy-2-(4-pyridinylamino)benzoyl]piperidineYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[5-Methoxy-2-(4-pyridinylamino)benzoyl]piperidine (Example 30b) (9.2 g) was dissolved in 100 ml of methylene dichloride. To this solution was added dropwise 80 ml of boron tribromide solution (0.8M in methylene dichloride). The mixture was kept at room temperature overnight and the solvent removed at reduced pressure. The residue was made basic with aqueous potassium carbonate and the solid product collected by filtration. The product was dissolved in methanol and acetonitrile added to produce 4.9 g of 1-[5-hydroxy-2-(4-pyridinylamino)benzoyl]piperidine. A further recrystallization from methanol gave a sample with m.p. 242°-243° C.(decompn.).

Workup

  1. customthe solvent removed at reduced pressure
  2. filtrationthe solid product collected by filtration
  3. dissolutionThe product was dissolved in methanol
  4. additionacetonitrile added

Sources & evidence

ORD record
ord-00f2f8924f234895ae8b88ec613b5bd8
Source dataset
uspto-grants-1986_09
Patent number
US04610991

Reaction notes

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