Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276585Notes

Reaction equation

HRID 276585 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5](C#N)(C)[CH:6]([CH3:8])[N:7]=1.[C:12]([C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[S:22])=[N:16][CH:15]1[CH3:23])#[N:13].[OH:25]CCN.Cl.Cl[CH2:31][C:32]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33]1>>[OH:25][CH2:8][C:6]1([NH2:7])[CH2:2][CH2:3][CH2:4][CH2:5]1.[C:12]([C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([N:20]=[C:21]2[S:22][CH2:31][C:32]3([CH2:36][CH2:35][CH2:34][CH2:33]3)[NH:37]2)=[N:16][CH:15]1[CH3:23])#[N:13]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 18316286HCID 18316286, compoundHCID 18316508HCID 18316508, compound2×HCID 699924851-(Chloromethyl)cyclopentan-1-amine hydrochloride2×

Product 2

HCID 663071-AminocyclopentanemethanolHCID 178433126HCID 178433126, compound

Procedure

6-Amino-3-cyano-2,3-dimethylpyridine was converted to 3-cyano-2,3-dimethyl-6-pyridyl isothiocyanate according to Method A2c. 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 3-cyano-2,3-dimethyl-6-pyridyl isothiocyanate according to Method C1e to give 2-(3-cyano-2,3-dimethyl-6-pyridylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2h to give 2-(5-bromothienylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-9a0129067dd145cebdb3891ed287fc7e
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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