Hydrochloric Acid → N-(indan-2-yl)-5-hydroxypentanamide

HRID 1942411Notes

Reaction equation

HRID 1942411 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].Cl.[NH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1.Cl.[C:17]1(=[O:23])[O:22][CH2:21][CH2:20][CH2:19][CH2:18]1>ClCCCl.ClC(Cl)C.CCN(CC)CC>[CH2:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH:7]1[NH:6][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][OH:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10953Delta-ValerolactoneHCID 1227642-Aminoindan hydrochlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 66937348N-(indan-2-yl)-5-hydroxypentanamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

A solution of 2.7 mL (18.75 mmol) of Et3N in 5 mL of 1,2-dichloroethane was added drop by drop under ice cooling to a suspension of 1.85 g (13.75 mmol) AlCl3 in 10 mL of dichloroethane. At room temperature a solution of 2.33 g (13.75 mmol) 2-aminoindane HCl (and Et3N for the solvation of the hydrochloride) and 1.16 mL (12.5 mmol) delta-valerolactone in 7.5 mL 1,2-dichloroethane was added to the mixture. After one hour of stirring at room temperature the mixture was quenched with ice water and stirred for another 30 minutes. The suspension was filtered by Celite. After adding of dichloromethane, separating of the organic layer, washing it with water, drying it with Na2SO4 and evaporating of the solvent, followed.

Workup

  1. customwas quenched with ice water
  2. stirringstirred for another 30 minutes
  3. filtrationThe suspension was filtered by Celite
  4. additionAfter adding of dichloromethane
  5. customseparating of the organic layer
  6. washwashing it with water
  7. dry with materialdrying it with Na2SO4
  8. customevaporating of the solvent

Sources & evidence

ORD record
ord-92e74bda7f5944ae9a5ed04781381ee4
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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