1-Bromo-3-chloropropane → HCID 18766912, compound

HRID 481036Notes

Reaction equation

HRID 481036 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]2=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][CH2:26][CH2:27][Cl:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:25][CH2:26][CH2:27][Cl:28])[C:15]2=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 13046891tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 18766912HCID 18766912, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of Compound 9 (1.7 g, 5.3 mM), as prepared in Example 9, bromopropylchloride (5.3 ml, 5.3 mM) and cesium carbonate (3.5 g, 10.6 mM) in acetone (60 ml) was stirred at reflux for 24 hours then cooled to RT. The acetone was removed under reduced pressure, the residue diluted with water (60 ml) and the aqueous mixture was extracted with ethyl acetate (2×60 ml). The combined ethyl acetate layers were dried over MgSO4 and evaporated in vacuo to give the product (2.1 g, 100%) as an oil that solidified on standing. m/z (MH+) 393.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe acetone was removed under reduced pressure
  3. additionthe residue diluted with water (60 ml)
  4. extractionthe aqueous mixture was extracted with ethyl acetate (2×60 ml)
  5. dry with materialThe combined ethyl acetate layers were dried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-53b1451c7d1c4581ba095cad589fbe82
Source dataset
uspto-grants-2003_11
Patent number
US06653478B2

Reaction notes

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