Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276551Notes

Reaction equation

C([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])(C)(C)C.I[C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15](C(C)(C)C)[CH:14]=1.NC1C=CC=CC=1.IC1C=CC(N=C=S)=C(C(C)(C)C)C=1.[OH:45]CCN.O=S(Cl)[Cl:51]>>[NH2:7][C:6]1([CH2:5][OH:45])[CH2:8][CH2:9][CH2:10][CH2:11]1.[ClH:51].[NH2:17][C:16]1([CH2:15][Cl:51])[CH2:14][CH2:13][CH2:19][CH2:18]1

Participants

Reactant 6

HCID 700Ethanolamine

HCID 6115Aniline

HCID 24386Thionyl Chloride

HCID 805742-tert-Butylaniline

HCID 121603822-Tert-butyl-4-iodoaniline

HCID 183162384-Iodo-2-tert-butylphenyl isothiocyanate

Product 2

HCID 663071-Aminocyclopentanemethanol

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

Procedure

2-tert-Butylaniline was converted to 4-iodo-2-tert-butylaniline according to Method A5a. The aniline was converted to 4-iodo-2-tert-butylphenyl isothiocyanate according to Method A2b. 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 4-iodo-2-tert-butylphenyl isothiocyanate according to Method C1a to give 2-(4-iodo-2-tert-butylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 3-cyclopentyl-2-(4-iodo-2-tert-butylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The phenyl iodide was reacted with CuCN according to Method D7a to afford 3-cyclopentyl-2-(4-cyano-2-tert-butylphenylimino)-1-thia-3-azaspiro[4.4]nonane.

Sources & evidence

ORD record: ord-fe68bad794bc4f839c6bdd4c75073bc6
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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