1-Bromo-3-chloropropane → 2-chloro-5-[3-chloropropoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085635Notes

Reaction equation

HRID 2085635 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:30][CH2:31][CH2:32][Cl:33]>C(O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:30][CH2:31][CH2:32][Cl:33])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)=[O:5]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 227314932-Chloro-5-hydroxy-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 227314912-chloro-5-[3-chloropropoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-5-hydroxy-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (WO 99/29661) (0.48 g) in ethanol (5 ml) was added caesium carbonate (0.977 g) and reaction mixture heated to 85° C. for 10 min. before addition of 1-bromo-3-chloropropane (0.74 ml). Heating was continued for 24 h before cooling to room temperature and concentration under reduced pressure. The residue was dissolved in ethyl acetate and washed with water(twice), then with KHSO4 solution and brine. The organics were dried (MgSO4), concentrated and the residue purified by silica gel chromatography (eluting with 20% ethyl acetate in isohexanes) to deliver the sub-title compound as a pale yellow foam (0.50 g).

Workup

  1. temperatureHeating
  2. concentrationconcentration under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water(twice)
  5. dry with materialThe organics were dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue purified by silica gel chromatography (eluting with 20% ethyl acetate in isohexanes)

Sources & evidence

ORD record
ord-bb78f2a6fbfd453e8660408017bb51e6
Source dataset
uspto-grants-2004_04
Patent number
US06720452B2

Reaction notes

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