Triethylamine → (3-Bromo-2-oxo-piperidin-1-yl)benzoic acid benzyl ester

HRID 1374077

Reaction equation

HRID 1374077 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13](N)=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:20](CC)CC)C.[Br:25][CH:26]([CH2:30][CH2:31][CH2:32]Br)[C:27](Cl)=[O:28].[OH-].[Na+].C(=O)([O-])O.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:20]1[CH2:32][CH2:31][CH2:30][CH:26]([Br:25])[C:27]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 98488Benzyl p-aminobenzoateHCID 110121401-Butanaminium, N,N,N-tributyl-, carbonic acid (1:1)HCID 1118503241339-29-1

Product 1

HCID 69484348(3-Bromo-2-oxo-piperidin-1-yl)benzoic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

45.5 g (0.2 mol) of 4-aminobenzoic acid benzyl ester and 30.6 ml (0.22 mol) of triethylamine are dissolved in 200 ml of methylene chloride and added in drops within 45 minutes at 0° C. to a solution of 55.3 g (0.2 mol) of 2,5-dibromovaleric acid chloride (Okawara et al. Chem. Pharm. Bull. (1982), (30), 1225) in 200 ml of methylene chloride, and it is stirred for 18 hours at room temperature. The reaction mixture is now added in drops at 0° C. to a solution of 400 ml of aqueous 32% sodium hydroxide and 2 g of tetrabutylammonium hydrogen carbonate (about 15 minutes), and it is stirred for 30 minutes. Then, the phases are separated, and the aqueous phase is extracted three times with 200 ml of dichloromethane each. The organic phases are dried on sodium sulfate, the solution is evaporated to the dry state and chromatographed on silica gel (methylene chloride). The fractions that contain the product are combined and concentrated by evaporation.

Workup

  1. stirringis stirred for 30 minutes
  2. customThen, the phases are separated
  3. extractionthe aqueous phase is extracted three times with 200 ml of dichloromethane each
  4. customThe organic phases are dried on sodium sulfate
  5. customthe solution is evaporated to the dry state
  6. customchromatographed on silica gel (methylene chloride)
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c1d6eea1a0cb40208c3684a07952486d
Source dataset
uspto-grants-2007_01
Patent number
US07164016B2

Linked notes

Loading…