Ethanolamine → 1-Oxa-4-azaspiro[4.5]decane

HRID 276329Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH2:4].[C:5]1(=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>>[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[NH:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 700Ethanolamine

HCID 7967Cyclohexanone

Product 1

HCID 2785591-Oxa-4-azaspiro[4.5]decane

Procedure

2-Hydroxyethylamine and cyclohexanone were reacted according to Method B4a, Step 1 to afford 4-aza-1-oxaspiro[4.5]decane. The oxazolidine was reduced according to method B4a, Step 2 to afford N-cyclohexyl-N-(2-hydroxyethyl)amine. The alcohol was reacted with SOCl2 according to Method B7c to afford N-cyclohexyl-N-(2-chloroethyl)amine. The amine was reacted with 2-methoxy-4-nitrophenyl isothiocyanate according to Method C1d to afford 2-(2-methyl-4-nitrophenylimino)-3-cyclohexyl-1,3-thiazolidine.

Sources & evidence

ORD record: ord-8cbce34288444be9a1d8f155cc6b2672
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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