Sodium Hydroxide → HCID 22004803, compound

HRID 324625Notes

Reaction equation

HRID 324625 reaction equation
Cl.C(N=C=NC[CH2:8][CH2:9]N(C)C)C.O.[OH:14]N1C2C=CC=CC=2N=N1.[NH2:24][C:25]1[C:26]([O:37][CH3:38])=[CH:27][CH:28]=[C:29]2[C:33]=1[CH:32]([CH2:34][CH2:35][NH2:36])[CH2:31][CH2:30]2.[OH-].[Na+]>CN(C)C=O.O.C(O)(=O)C>[NH2:24][C:25]1[C:26]([O:37][CH3:38])=[CH:27][CH:28]=[C:29]2[C:33]=1[CH:32]([CH2:34][CH2:35][NH:36][C:8](=[O:14])[CH3:9])[CH2:31][CH2:30]2

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22004827HCID 22004827, compound

Product 1

HCID 22004803HCID 22004803, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

In substantially the same manner as in Reference Example 38, 2-(7-amino-6-methoxyindan-1-yl)ethylamine was produced from (E)-(7-amino-6-methoxyindan1-ylidene) acetonitrile. The crude product thus obtained was used, without further purification, for the reaction described below. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.3 g, 17.2 mmol.) and 1-hydroxybenzotriazole monohydrate (2.2 g, 14.4 mmol.) were suspended in N,N-dimethylformamide (30 mL). To the suspension was added, under ice-cooling, acetic acid (0.65 mL). This reaction mixture was stirred for one hour at room temperature, which was again cooled with ice. To the mixture was added dropwise a solution of the above-mentioned crude 2-(7-amino-6-methoxyindan-1-yl) ethylamine in N,N-dimethylformamide (10 mL). The mixture was stirred for 30 minutes, which was poured into water. The mixture was subjected to extraction with ethyl acetate. From the organic layer was extracted the hydrochloride with 2N hydrochloric acid. Then, the aqueous layer thus obtained was adjusted to pH 10 with a 4N aqueous solution of sodium hydroxide. From the aqueous layer, the organic matter was extracted with ethyl acetate, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate:ethanol=10:1) to afford the title compound (yield 1.6 g, 66%).

Workup

  1. customwas used, without further purification, for the reaction
  2. additionTo the suspension was added, under ice-
  3. temperaturecooling
  4. temperaturewhich was again cooled with ice
  5. stirringThe mixture was stirred for 30 minutes
  6. extractionThe mixture was subjected to extraction with ethyl acetate
  7. extractionFrom the organic layer was extracted the hydrochloride with 2N hydrochloric acid
  8. customThen, the aqueous layer thus obtained
  9. extractionFrom the aqueous layer, the organic matter was extracted with ethyl acetate, which
  10. dry with materialwas dried over anhydrous magnesium sulfate
  11. distillationby distilling off the solvent under reduced pressure
  12. customThe residue was purified by means of silica gel column chromatography (ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record
ord-ade7307cbcb448c0b34ee909c86a7627
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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