Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276555Notes

Reaction equation

C([C:3]1[CH:9]=[C:8]([N+]([O-])=O)[CH:7]=[CH:6][C:4]=1[NH2:5])C.C([C:15]1[CH:20]=[C:19]([N+]([O-])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]=C=S)C.OCCN.O=S(Cl)[Cl:33]>>[NH2:5][C:4]1([CH2:3][OH:22])[CH2:6][CH2:7][CH2:8][CH2:9]1.[ClH:33].[NH2:24][C:16]1([CH2:15][Cl:33])[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

Reactant 4

HCID 700Ethanolamine

HCID 24386Thionyl Chloride

HCID 148190092-Ethyl-4-nitroaniline

HCID 183164182-Ethyl-4-nitrophenyl isothiocyanate

Product 2

HCID 663071-Aminocyclopentanemethanol

HCID 699924851-(Chloromethyl)cyclopentan-1-amine hydrochloride

Procedure

2-Ethylaniline was converted to 2-ethylacetanilide according to Method A2a, Step 1. The acetanilide was converted to 2-ethyl-4-nitroacetanilide according to Method A2a, Step 2. The acetanilide was deprotected according to Method A2a, Step 3 to give 2-ethyl-4-nitroaniline. The aniline was converted to 2-ethyl-4-nitrophenyl isothiocyanate according to Method A2a, Step 3. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7a to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 2-ethyl-4-nitrophenyl isothiocyanate according to Method C1a to give 2-(2-ethyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford 1-isobutyl-2-(2-ethyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record: ord-dad846e504b545fdafa17784c1a38dcf
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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