Sodium Carbonate → HCID 67836505, compound

HRID 741569Notes

Reaction equation

HRID 741569 reaction equation
[CH2:1]1[CH:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH:2]1[CH2:11][O:12][C:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32](=[O:34])[CH3:33].C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[C:32]([CH2:33][N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([C:13]([O:12][CH2:11][CH:2]2[CH2:3][CH2:4][N:5]3[CH:10]([CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:1]2)=[O:14])=[CH:16]1)(=[O:34])[CH3:31]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 131719520Quinolizidin-2-ylmethylindole-3-carboxylate

Product 1

HCID 67836505HCID 67836505, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of eq-quinolizidin-2-ylmethylindole-3-carboxylate (E9b) (300 mg, 0.96 mmol) in acetone (10 ml) was treated with anhydrous potassium carbonate (270 mg, 2 mmole) and bromoacetone (150 mg, 1.1 mmole) and kept at room temperature for 3 days. The mixture was treated with 10% Na2CO3 solution (10 ml) and extracted with ethyl acetate (2×25 ml). The combined extracts were dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with ethyl acetate/methanol (95:5). The pale yellow oil obtained was crystallised from ether to afford the title compound (E31) as a beige solid (14 mg) mp 139°-1420C.

Workup

  1. extractionextracted with ethyl acetate (2×25 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue chromatographed on silica gel eluting with ethyl acetate/methanol (95:5)
  5. customThe pale yellow oil obtained
  6. customwas crystallised from ether

Sources & evidence

ORD record
ord-7d1cacaba8d24ff9be37c6d08316a810
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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