Acetamide → 1-Aminocyclopentanemethanol

HRID 276609Notes

Reaction equation

HRID 276609 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].CC1C=CC=C(NC(C)=[O:19])C=1C.C(N)(=O)C.CC1C(C)=CC=C([N+:35]([O-:37])=[O:36])C=1N.NC1C=CC=CC=1.OCCN.Cl.ClCC1(N)CCCC1.C[C:59]1[C:64](C)=[CH:63][CH:62]=[C:61]([N+]([O-])=O)[C:60]=1[N:69]=[C:70]=[S:71]>>[OH:19][CH2:5][C:3]1([NH2:4])[CH2:2][CH2:8][CH2:7][CH2:6]1.[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([N+:35]([O-:37])=[O:36])[C:3]=1[N:4]=[C:70]1[S:71][CH2:61][C:60]2([CH2:59][CH2:64][CH2:63][CH2:62]2)[NH:69]1

Participants

10

Reactant 8

HCID 178AcetamideHCID 700EthanolamineHCID 6115AnilineHCID 68932,3-DimethylanilineHCID 86562',3'-AcetoxylidideHCID 5971662,3-Dimethyl-6-nitroanilineHCID 183164822,3-Dimethyl-6-nitrophenyl isothiocyanateHCID 699924851-(Chloromethyl)cyclopentan-1-amine hydrochloride2×

Product 2

HCID 663071-AminocyclopentanemethanolHCID 178426721HCID 178426721, compound

Procedure

2,3-Dimethylaniline was protected as 2,3-dimethylacetanilide according to Method A2a, step 1. The acetamide was converted to 2,3-dimethyl-6-nitroaniline, then deprotected according to Method A2a, step 2. The aniline was converted to 2,-dimethyl-6-nitrophenyl isothiocyanate according to Method A2a, step 3. 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 cyclopentyl bromide according to Method D2b to give 2-(2,3-dimethyl-6-nitrophenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-4668162cb9304d0c8dedc64c9b463a9c
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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