Potassium Hydroxide → HCID 54353232, compound

HRID 1357048Notes

Reaction equation

HRID 1357048 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([C:23]([NH2:25])=[O:24])=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH2:28]([CH:30]1[O:32][CH2:31]1)Br>CC(C)=O>[CH:19]1([CH2:23][NH:25][CH2:28][CH:30]([OH:32])[CH2:31][NH:25][C:23]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([N:11]2[CH2:10][CH2:9][CH:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:13][CH2:12]2)=[CH:22]3)=[O:24])[CH2:20][CH2:21][CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 18430EpibromohydrinHCID 54483006HCID 54483006, compound

Product 1

HCID 54353232HCID 54353232, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The title compound was prepared according to scheme 7. To an ice-cold solution of 1.0 g (3.0 mmol) of 4-benzylpiperidinyl indole-5-carboxamide in acetone was added 15 mmol of powdered KOH followed by 3.0 mmol of epibromohydrin and the mixture was stirred for 30 min. The mixture was filtered and the solution was evaporated. The residue was dissolved in ethyl acetate, washed with water, dried and evaporated. After purification by silica gel column chromatography 435 mg of epoxide was obtained. MS (M+ 373).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solution was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customAfter purification by silica gel column chromatography 435 mg of epoxide
  8. customwas obtained

Sources & evidence

ORD record
ord-5d52be3b694a43d283b47bf973236982
Source dataset
uspto-grants-2003_07
Patent number
US06589954B1

Reaction notes

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