Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276620

Reaktionsgleichung

Reaktionsgleichung von HRID 276620
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[S:18])=[C:12]([CH3:19])[CH:11]=1)#[N:9].[OH:20]C[CH2:22][NH2:23].Cl.Cl[CH2:26][C:27]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28]1>>[C:8]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([CH3:19])[CH:11]=1)#[N:9].[OH:20][CH2:7][C:2]1([NH2:1])[CH2:3][CH2:4][CH2:5][CH2:6]1.[C:22]([C:6]1[CH:5]=[CH:4][C:19]([C:12]2[CH:11]=[CH:10][CH:15]=[CH:14][C:13]=2[N:16]=[C:17]2[S:18][CH2:26][C:27]3([CH2:31][CH2:30][CH2:29][CH2:28]3)[NH:32]2)=[CH:2][CH:7]=1)#[N:23]

Komponenten

7

Edukt 4

HCID 700EthanolamineHCID 6115AnilineHCID 183162994-Cyano-2-methylphenyl isothiocyanate2×HCID 699924851-(Chloromethyl)cyclopentan-1-amine hydrochloride2×

Produkt 3

HCID 663071-AminocyclopentanemethanolHCID 70103164-Amino-3-methylbenzonitrileHCID 1785095612-(4-Cyanophenylphenylimino)-3-thia-1-azaspiro[4.4]nonane

Versuchsvorschrift

4-Cyano-2-methylaniline was prepared according to Method A1a. The aniline was converted to 4-cyano-2-methylphenyl isothiocyanate according to Method A2b. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was converted to 1-chloromethylcyclopentanamine HCl salt according to Method B7e. 1-Chloromethylcyclopentanamine HCl salt was reacted with 4-cyano-2-methylphenyl isothiocyanate according to Method C1e to give 2-(4-cyanophenylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(4-cyano-2-methylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane. The nitrile was hydrolyzed according to Method D9a to afford 2-(4-carboxy-2-methylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Quellen und Nachweise

ORD-Eintrag
ord-be2fe4b724b24980a0d8ae8b7f51af2f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353006B1

Verknüpfte Notizen

Wird geladen…