2-Chloroethylamine → HCID 18316338, compound

HRID 276698

Reaction equation

HRID 276698 reaction equation
O=S(Cl)Cl.[CH:5]1([NH:11][C:12]2([CH2:17]Cl)[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.ClCCN.[CH3:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[N:33]=[C:34]=[O:35]>>[CH:5]1([N:11]2[C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:17][O:35][C:34]2=[N:33][C:25]2[CH:26]=[CH:27][C:28]([N+:30]([O-:32])=[O:31])=[CH:29][C:24]=2[CH3:23])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 133692-ChloroethylamineHCID 24386Thionyl ChlorideHCID 42964562-Methyl-4-nitrophenyl isocyanateHCID 183161661-(Cyclohexylamino)-1-(chloromethyl)cyclopentane

Product 1

HCID 18316338HCID 18316338, compound

Procedure

1-Aminocyclopentanecarboxylic acid was converted to the methyl ester according to Method B1c, Step 1. The ester reduced to 1-hydroxymethylcyclopentanamine according to Method B1c, Step 2. The hydroxyethylamine was reacted with cyclohexanone according to Method B4a, Step 1 to give 6-aza-13-oxadispiro[4.1.5.2]tetradecane. The oxazolidine was reduced according to Method B4a, Step 2 to give 1-(cyclohexylamino)-1-(hydroxymethyl)cyclopentane. The substituted 2-hydroxyethylamine was reacted with SOCl2 according to Method B7b to 1-(cyclohexylamino)-1-(chloromethyl)cyclopentane. The 2-chloroethylamine was reacted with 2-methyl-4-nitrophenyl isocyanate according to Method C4a to afford 1-cyclohexyl-2-(2-methyl-4-nitrophenylimino)-3-oxa-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-4bec818de8e34c649e9d1c55d689caf0
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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