Water → HCID 67328656, compound

HRID 2235006Notes

Reaction equation

HRID 2235006 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[O:5][CH:6]1[CH2:12][CH:11]2[NH:13][CH:8]([CH2:9][CH2:10]2)[CH2:7]1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)CC)C.[OH2:32]>CN(C)C=O>[C:4]([OH:32])(=[O:5])/[CH:14]=[CH:19]/[C:20]([OH:22])=[O:21].[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:13]1[CH:8]2[CH2:9][CH2:10][CH:11]1[CH2:12][CH:6]([O:5][C:4]1[CH:14]=[CH:15][C:16]([Cl:17])=[C:2]([Cl:1])[CH:3]=1)[CH2:7]2)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 11311791HCID 11311791, compound

Product 1

HCID 67328656HCID 67328656, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g of 3-(3,4-dichloro-phenoxy)-8-aza-bicyclo[3.2.1]octane in 75 ml of N,N-dimethylformamide was first added 1.8 ml of ethyl bromoacetate then 4.5 ml triethylamine. The reaction mixture was stirred overnight at room temperature, then poured into 200 ml of water. The mixture was extracted twice with 150 ml of diethyl ether, the organic phase was dried with sodium sulphate and evaporated into an oil. 5.5 g 94%. 1.5 g of the oil was dissolved in a mixture of ethyl acetate and methanol. The solution was added 0.5 g of fumaric acid and evaporated, the residue was trituated with diethyl ether. Yield 1.3 g 65% Mp. 127-130° C.

Workup

  1. extractionThe mixture was extracted twice with 150 ml of diethyl ether
  2. dry with materialthe organic phase was dried with sodium sulphate
  3. customevaporated into an oil
  4. dissolution1.5 g of the oil was dissolved in a mixture of ethyl acetate and methanol
  5. additionThe solution was added 0.5 g of fumaric acid
  6. customevaporated

Sources & evidence

ORD record
ord-7aa78dad142c495dae3ee803b5d03779
Source dataset
uspto-grants-2010_05
Patent number
US07713990B2

Reaction notes

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