Ethanol, 2-(cyclohexylamino)- → N-(2-chloroethyl)cyclohexanamine

HRID 276330Notes

Reaction equation

[CH:1]1([NH:7][CH2:8][CH2:9]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:13]>>[CH:1]1([NH:7][CH2:8][CH2:9][Cl:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 17827Ethanol, 2-(cyclohexylamino)-

HCID 24386Thionyl Chloride

Product 1

HCID 410533N-(2-chloroethyl)cyclohexanamine

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-4066b0a77d574dd1a4eb42462eeb6029
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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