Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276630Notes

Reaction equation

HRID 276630 reaction equation
[OH:1][CH2:2][CH2:3][NH2:4].O=S(Cl)Cl.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[S:18])=[C:12]([CH3:19])[CH:11]=1>>[OH:1][CH2:2][C:3]1([NH2:4])[CH2:12][CH2:11][CH2:10][CH2:15]1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]2[S:18][CH2:2][C:3]3([CH2:12][CH2:11][CH2:10][CH2:15]3)[NH:4]2)=[C:12]([CH3:19])[CH:11]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 24386Thionyl ChlorideHCID 879774-Bromo-1-isothiocyanato-2-methylbenzene

Product 2

HCID 663071-AminocyclopentanemethanolHCID 178422439HCID 178422439, compound

Procedure

1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was sequentially reacted with SOCl2 and 4-bromo-2-methylphenyl isothiocyanate according to Method C2a to give 2-(4-bromo-2-methylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method1 D2b to give 2-(4-bromo-2-methylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-fdcc42809fd44ce581b1776076721744
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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