Hydrochloric Acid → HCID 178519237, compound

HRID 486821Notes

Reaction equation

HRID 486821 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[CH:11]=[C:10]([C:12]2([C:21](OCC)=[O:22])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)[N:9]=[CH:8]1.C(OCC)(=O)C.Cl>C1COCC1>[NH:7]1[CH:11]=[C:10]([C:12]2([CH2:21][OH:22])[CH2:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:20]2)[N:9]=[CH:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 178468443HCID 178468443, compound

Product 1

HCID 178519237HCID 178519237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,8 g of LiAlH4 were added to 75 ml of dry tetrahydrofurane in nitrogen atmosphere. 15,0 g of ethyl 2,3-dihydro-2-(1H-imidazol-4-yl)-1H-indene-2-carboxylate (prepared according to EP 247764) were dissolved in 150 ml of dry THF and slowly added dropwise at room temperature. After the addition the mixture was stirred for 2 h at room temperature and then for an additional 2 h at +40° C. Excess of LiAlH4 was decomposed by slow addition of ethyl acetate. Then the mixture was poured into dilute hydrochloric acid. The aqueous solution was washed with methylene chloride and made alkaline with sodium hydroxide. The product was extracted in ethyl acetate. The precipitate formed during the extraction was filtered and washed several times with hot ethyl acetate and methylene chloride. The organic solutions were combined, dried and evaporated. The hydrochloride of the product was made in ethyl acetate by HCl-ethyl acetate, m.p. 181°-184° C.

Workup

  1. additionslowly added dropwise at room temperature
  2. additionAfter the addition the mixture
  3. waitfor an additional 2 h at +40° C
  4. washThe aqueous solution was washed with methylene chloride
  5. extractionThe product was extracted in ethyl acetate
  6. customThe precipitate formed during the extraction
  7. filtrationwas filtered
  8. washwashed several times with hot ethyl acetate and methylene chloride
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-f1344e85c3b94213810ac1c5abddbc12
Source dataset
uspto-grants-1994_03
Patent number
US05292887

Reaction notes

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