Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276586Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH2:4].O=S(Cl)Cl.[CH3:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[N:19]=[C:20]=[S:21]>>[OH:1][CH2:2][C:3]1([NH2:4])[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[N:19]=[C:20]1[S:21][CH2:2][C:3]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[NH:4]1

Participants

Reactant 3

HCID 700Ethanolamine

HCID 24386Thionyl Chloride

HCID 1456212-Methyl-4-nitrophenyl isothiocyanate

Product 2

HCID 663071-Aminocyclopentanemethanol

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

Procedure

1-(Hydroxymethyl)cyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was sequentially reacted with SOCl2 and 2-methyl-4-nitrophenyl isothiocyanate according to Method C2a to give 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with 1-bromo-2-ethylbutane according to Method D2a to afford 2-(2-methyl-4-nitrophenylimino)-1-(2-ethyl-1-butyl)-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record: ord-b5d177606b6944628403224115a0021e
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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