Ethanolamine → [1-(Cyclopentylamino)cyclopentyl]methanol

HRID 276628

Reaction equation

HRID 276628 reaction equation
[Cl:1]C1C(C)=C(C=CC=1)N.C(NC1C=CC=CC=1)=O.OCCN.[CH2:23]1[C:27]2([NH:35][C:30]3([CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:29][O:28]2)[CH2:26][CH2:25][CH2:24]1.O1CCNC1>>[ClH:1].[OH:28][CH2:29][C:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1.[CH:27]1([NH:35][C:30]2([CH2:29][OH:28])[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

7

Reactant 5

HCID 700EthanolamineHCID 68943-Chloro-2-methylanilineHCID 7671FormanilideHCID 5366831,3-OxazolidineHCID 1831628713-aza-6-oxadispiro[4.2.4.I]tridecane

Product 2

HCID 18316183[1-(Cyclopentylamino)cyclopentyl]methanolHCID 23143728(1-Aminocyclopentyl)methanol hydrochloride

Procedure

3-Chloro-2-methylaniline was converted to the 3-chloro-2-methylformanilide according to Method A3a, Step 1. The formanilide was converted to 3-chloro-2-methylphenyl isocyanide dichloride according to Method A3a, Step 2. 1-Hydroxymethylcyclopentanamine HCl salt was synthesized according to Method B1c. The 2-hydroxyethylamine was converted to 13-aza-6-oxadispiro[4.2.4. 1]tridecane according to Method B4d, Step 1. The oxazolidine was reductively opened according to Method B4d, Step 2 to give 1-(cyclopentylamino)-1-(hydroxymethyl)cyclopentane. The substituted 2-hydroxyethylamine was converted to 1-(cyclopentylamino)-1-(thioacetylmethyl)cyclopentane according to Method C6c, Step 1. The thioacetate was hydrolyzed according to Method C6c, Step 2 to give 1-(cyclopentylamino)-1-(thiomethyl)cyclopentane. The 2-thioethylamine was reacted with 3-chloro-2-methylphenyl isocyanide dichloride according to Method C6c to afford 2-(3-chloro-2-methylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-0228c29b52a64fada7ab78eb86f55c68
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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