Sodium Chloride → HCID 19036383, compound

HRID 264559Notes

Reaction equation

HRID 264559 reaction equation
[N:1]1([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:5]=[CH:4][C:3]2[CH2:6][CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:2]1=2.[OH-:21].[K+].[Cl-].[Na+].[CH2:25]([OH:28])[CH2:26]O.[OH2:29]>>[C:18]([OH:20])(=[O:29])/[CH:19]=[CH:26]/[C:25]([OH:28])=[O:21].[N:1]1([CH2:15][CH2:16][NH2:17])[CH:5]=[CH:4][C:3]2[CH2:6][CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:2]1=2

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036566HCID 19036566, compoundHCID 20437942Ethylene glycol water

Product 1

HCID 19036383HCID 19036383, compoundYield 72%

Procedure

1.80 g of N-[2-(1,4,5,6-tetrahydro-benzo[6,7]cyclohepta[1,2-b]pyrrol-1-yl)-ethyl]-acetamide were heated to 140° for 24 hours under argon in 18 ml of ethylene glycol/water 2:1 in the presence of 1.0 g of potassium hydroxide. The reaction mixture was left to cool and was poured into 140 ml of semi-concentrated sodium chloride solution. The mixture was extracted three times with diethyl ether and the combined extracts were washed once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The thus-obtained oil was chromatographed on 60 g of silica gel with methylene chloride/methanol 19:1. The crude product was dissolved in 5 ml of diethyl ether and treated with 505 mg of fumaric acid in 10 ml of diethyl ether. The crystals were filtered off and recrystallized from 50 ml of ethyl acetate/ethanol 2:1. 1.65 g (72%) of 2-(1,4,5,6-tetrahydro-benzo[6,7]cyclohepta[1,2-b]pyrrol-1-yl)-ethylamine fumarate (1:1) were obtained as white crystals with m.p. 175°-176°.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. extractionThe mixture was extracted three times with diethyl ether
  4. washthe combined extracts were washed once with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe thus-obtained oil was chromatographed on 60 g of silica gel with methylene chloride/methanol 19:1
  9. dissolutionThe crude product was dissolved in 5 ml of diethyl ether
  10. additiontreated with 505 mg of fumaric acid in 10 ml of diethyl ether
  11. filtrationThe crystals were filtered off
  12. customrecrystallized from 50 ml of ethyl acetate/ethanol 2:1

Sources & evidence

ORD record
ord-57521d106386498c8644a1a0cecfc4a8
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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