2-Indanone → HCID 13132281, compound

HRID 2372583Notes

Reaction equation

HRID 2372583 reaction equation
[ClH:1].[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])[CH3:3].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+].[CH2:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][C:20]1=O>CO>[ClH:1].[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH:8][CH:20]1[CH2:19][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)[CH3:3]

Participants

6

Reactant 4

HCID 119832-IndanoneHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13132281HCID 13132281, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a solution of 13 g of 2-indanone in 100 ml of methanol, there is dissolved 13 g of β-alanine ethyl ester hydrochloride, and, with ice cooling and stirring, 6.5 g of sodium cyanoborohydride is added portionwise. After standing at room temperature overnight, the mixture is poured into 500 ml of ice water, made alkaline with sodium hydrogen carbonate and extracted with 200 ml of chloroform. The extract is washed with water, and dried, followed by distilling off chloroform under reduced pressure. To the residue, 10 ml of 20% ethanolic hydrochloric acid and 50 ml of ethyl ether are added successively, and the mixture is allowed to stand at room temperature. The resulting precipitate is collected by filtration and dried to give 10 g of N-(indan-2-yl)-β-alanine ethyl ester hydrochloride as colorless scales melting at 150°-151° C.

Workup

  1. extractionextracted with 200 ml of chloroform
  2. washThe extract is washed with water
  3. customdried
  4. distillationby distilling off chloroform under reduced pressure
  5. additionTo the residue, 10 ml of 20% ethanolic hydrochloric acid and 50 ml of ethyl ether are added successively
  6. customto stand at room temperature
  7. filtrationThe resulting precipitate is collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-07ee5eec962f407fb12dd856336735c2
Source dataset
uspto-grants-1992_03
Patent number
US05098892

Reaction notes

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