1-Adamantaneacetic acid → HCID 9797873, compound

HRID 1066238Notes

Reaction equation

HRID 1066238 reaction equation
[C:1]12([CH2:11][C:12]([OH:14])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl.CN(C)CCCN=C=NCC.[NH2:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32]([CH3:37])=[C:31]2[CH3:38]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:37][C:32]1[NH:33][C:34]2[C:30]([C:31]=1[CH3:38])=[CH:29][C:28]([NH:27][C:12](=[O:14])[CH2:11][C:1]13[CH2:2][CH:3]4[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]4)[CH2:10]1)[CH2:8]3)=[CH:36][CH:35]=2

Participants

6

Reactant 3

HCID 1232211-Adamantaneacetic acidHCID 2586882,3-dimethyl-1H-indol-5-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 9797873HCID 9797873, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-adamantaneacetic acid (0.30 g) in dichloromethane (10 ml) were added 4-dimethylaminopyridine (0.19 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.30 g). The reaction mixture was stirred for 0.5 hour before addition of 5-amino-2,3-dimethylindole (0.25 g). Stirring was then continued overnight at ambient temperature. The next day the reaction mixture was washed with dilute hydrochloric acid, water and brine, dried over sodium sulphate (Na2SO4) and finally concentrated under reduced pressure to leave a residue. Purification of the residue by silica gel chromatography, eluting with 40% ethyl acetate in isohexanes, gawe the title compound as a white solid (0.14 g).

Workup

  1. washThe next day the reaction mixture was washed with dilute hydrochloric acid, water and brine
  2. dry with materialdried over sodium sulphate (Na2SO4)
  3. concentrationfinally concentrated under reduced pressure
  4. customto leave a residue
  5. customPurification of the residue by silica gel chromatography
  6. washeluting with 40% ethyl acetate in isohexanes

Sources & evidence

ORD record
ord-0328cb1873af46e6bc9d574253e554b7
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Reaction notes

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