HCID 20537491, compound → HCID 20537472, compound

HRID 1155689Notes

Reaction equation

HRID 1155689 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH2:8][C:7]([C:12]3[CH:20]=[CH:19][CH:18]=[C:17]4[C:13]=3[CH:14]=[CH:15][NH:16]4)(O)[CH2:6]2)[CH2:3][CH2:2]1>Cl.O>[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH:8]=[C:7]([C:12]3[CH:20]=[CH:19][CH:18]=[C:17]4[C:13]=3[CH:14]=[CH:15][NH:16]4)[CH2:6]2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 20537491HCID 20537491, compound

Product 1

HCID 20537472HCID 20537472, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 10 g of the product of Example 25 in 300 ml of 1 N hydrochloric acid was refluxed for 6 hours and was then cooled to room temperature and was diluted with 300 ml of water. The mixture was extracted with ethyl acetate and the organic phase was washed with aqueous sodium chloride and evaporated to dryness under reduced pressure. The 9.1 g of residue were chromatographed over silica gel and eluted with a 95-5 chloroform-methanol mixture to obtain 5.4 g of 4-[1-cyclopropylmethyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole with an Rf=0.10.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with aqueous sodium chloride
  3. customevaporated to dryness under reduced pressure
  4. customThe 9.1 g of residue were chromatographed over silica gel
  5. washeluted with a 95-5 chloroform-methanol mixture

Sources & evidence

ORD record
ord-14c120ff24db456ba73cec6889c0c28c
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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