Bromocyclopentane → HCID 21914413, compound

HRID 2421372Notes

Reaction equation

HRID 2421372 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Br[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 21914372HCID 21914372, compound

Product 1

HCID 21914413HCID 21914413, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-3-(2-{piperidin-1-yl}ethoxy)phenol (1.5 g), bromocyclopentane (0.59 ml) and anhydrous potassium carbonate (1.04 g) were stirred and heated at 80° C. in dimethylformamide for 18 h. The mixture was partitioned between ethyl acetate (100 ml) and water (70 ml). The aqueous was extracted further with ethyl acetate (100 ml) and the combined organics were washed with 2N sodium hydroxide solution (50 ml), water (50 ml), brine (50 ml), dried (MgSO4) and evaporated to give the product as an oil (1.5 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate (100 ml) and water (70 ml)
  2. extractionThe aqueous was extracted further with ethyl acetate (100 ml)
  3. washthe combined organics were washed with 2N sodium hydroxide solution (50 ml), water (50 ml), brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-61d03589b4514c1cac8bb3719a4bd6cf
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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