Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276563Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[C:14]([CH3:15])=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:11][C:10]=1[N:19]=C=S.[OH:22]CCN.O=S(Cl)[Cl:28]>>[CH3:8][C:9]1[C:14]([CH3:15])=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:11][C:10]=1[NH2:19].[NH2:1][C:2]1([CH2:3][OH:22])[CH2:7][CH2:6][CH2:5][CH2:4]1.[ClH:28].[NH2:1][C:2]1([CH2:3][Cl:28])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

Reactant 4

HCID 700Ethanolamine

HCID 6115Aniline

HCID 24386Thionyl Chloride

HCID 183160152,3-Dimethyl-4-nitrophenyl isothiocyanate

Product 3

HCID 663071-Aminocyclopentanemethanol

HCID 70990352,3-Dimethyl-4-nitroaniline

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

Procedure

2,3-Dimethyl-4-nitroaniline was synthesized as described in Method A4a. The aniline was converted into 2,3-dimethyl-4-nitrophenyl isothiocyanate as described in method A2d. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7e to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 2,3-dimethyl-4-nitrophenyl isothiocyanate according to Method C1c to give 2-(2,3-dimethyl-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-isopropyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record: ord-d5c19f8b64314f149e08f78d123b643b
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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