Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276581Notes

Reaction equation

HRID 276581 reaction equation
C[C:2]1[C:8](C)=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].CC1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]([N+:19]([O-])=[O:20])[C:12]=1N.NC1C=CC=CC=1.[CH3:29][C:30]1[C:35]([CH3:36])=[CH:34][CH:33]=[C:32]([N+:37]([O-:39])=[O:38])[C:31]=1[N:40]=[C:41]=[S:42].OCCN.Cl.ClCC1(N)CCCC1>>[OH:20][CH2:5][C:3]1([NH2:4])[CH2:2][CH2:8][CH2:7][CH2:6]1.[CH3:29][C:30]1[C:35]([CH3:36])=[CH:34][CH:33]=[C:32]([N+:37]([O-:39])=[O:38])[C:31]=1[N:40]=[C:41]1[S:42][CH2:12][C:14]2([CH2:15][CH2:16][CH2:17][CH2:18]2)[NH:19]1

Participants

8

Reactant 6

HCID 700EthanolamineHCID 6115AnilineHCID 68932,3-DimethylanilineHCID 5971662,3-Dimethyl-6-nitroanilineHCID 183164822,3-Dimethyl-6-nitrophenyl isothiocyanate2×HCID 699924851-(Chloromethyl)cyclopentan-1-amine hydrochloride2×

Product 2

HCID 663071-AminocyclopentanemethanolHCID 178426721HCID 178426721, compound

Procedure

2,3-Dimethylaniline was converted to 2,3-dimethyl-6-nitroaniline according to Method A4a. The aniline was converted to 2,3-dimethyl-6-nitrophenyl isothiocyanate according to Method A2d. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was converted to 1-chloromethylcyclopentanamine HCl salt according to Method B7e. 1-Chloromethylcyclopentanamine HCl salt was reacted with 2,3-dimethyl-6-nitrophenyl isothiocyanate according to Method C1e to give 2-(2,3-dimethyl-6-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2b to afford 2-(2,3-dimethyl-6-nitrophenylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-ee0f7107f47540a5b931a53d3863e592
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…