Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276602Notes

Reaction equation

HRID 276602 reaction equation
[OH:1][CH2:2][CH2:3][NH2:4].Cl.Cl[CH2:7][C:8]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]=[C:25]=[S:26]>>[OH:1][CH2:2][C:3]1([NH2:4])[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]=[C:25]1[S:26][CH2:7][C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[NH:13]1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 1456212-Methyl-4-nitrophenyl isothiocyanateHCID 699924851-(Chloromethyl)cyclopentan-1-amine hydrochloride2×

Product 2

HCID 663071-AminocyclopentanemethanolHCID 1784287362-(2-Methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

Procedure

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 2-methyl-4-nitrophenyl isothiocyanate according to Method C1e to give 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with 2-(2-bromoethyl)-1,3-dioxane according to Method D2e to give 2-(2-methyl-4-nitrophenylimino)-1-(2-(1,3-dioxan-2-yl)ethyl)-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-ba26e8b6d63047629ae9883a37ecf4af
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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