2-Indanone → HCID 13132281, compound

HRID 621167Notes

Reaction equation

HRID 621167 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 ester 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 ester are added successively
  6. customto stand at room temperature
  7. filtrationThe resulting precipitate is collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-ce1ffa443df74c26a1d97970469bfa49
Source dataset
uspto-grants-1989_04
Patent number
US04822818

Reaction notes

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