Water → HCID 63681192, compound

HRID 2042008Notes

Reaction equation

HRID 2042008 reaction equation
[NH:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH2:18][C:19](Br)=[O:20].O>C(Cl)Cl>[Br:17][CH2:18][C:19]([N:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 92911Decahydroquinoline

Product 1

HCID 63681192HCID 63681192, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled suspension of 2.15 g (15 mmol) of decahydroquinoline, 5.20 g (37.5 mmol) of potassium carbonate in 30 ml of methylene chloride was added 3.10 g (15 mmol) of bromoacetylbromide. Then the reaction mixture was stirred at RT for 20 h, Water was added, the mixture extracted by methylene chloride, the organic phase washed by water, dried over sodium sulphate and evaporated to dryness. Flash chromatography using methylene chloride as eluant afforded 2.6 g of compound as uncolorless oil.

Workup

  1. extractionthe mixture extracted by methylene chloride
  2. washthe organic phase washed by water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4206bf68dce44416862f5e4f5709cf79
Source dataset
uspto-grants-2013_11
Patent number
US08586577B2

Reaction notes

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