Sodium Hydroxide → HCID 20030186, compound

HRID 1721954Notes

Reaction equation

HRID 1721954 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=O)[CH:16]=[CH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH:20]=[CH:21][NH:22]2)([CH3:4])[CH3:3].[Cl:28]N1C(=O)CCC1=O.[OH-].[Na+]>C(O)(=O)C.O>[Cl:28][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[CH:26][C:18]=2[CH2:17][CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6][NH:5][C:2]([CH3:4])([CH3:3])[CH3:1])[NH:22][CH:21]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 53770388HCID 53770388, compound

Product 1

HCID 20030186HCID 20030186, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4.74 g of the product of Example 9 in 43 ml of acetic acid was added with stirring under an inert atmosphere to 2.17 g of N-chlorosuccinimide over 40 minutes and the mixture was diluted with water and iced. The mixture was made alkaline by addition of 32% sodium hydroxide solution and was extracted with ethyl acetate. The organic phase was washed with water, dried over a deshydrant, filtered and evaporated to dryness. The residue was chromatographed over silica and eluted with a 9-1 ethyl acetate-triethylamine mixture to obtain 3.76 g of N-[2-{2-(3-[3-chloro-1H-indol-4-yl]-propyl)-phenoxy}-ethyl]-2-methyl-2-propanamine.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried over a deshydrant
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed over silica
  7. washeluted with a 9-1 ethyl acetate-triethylamine mixture

Sources & evidence

ORD record
ord-1ea155ed39d4492cb3798442fd6431e9
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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