2-Chloroethylamine → 1-Cyclobutyl-2-(2-methyl-4-nitrophenylimino)-3-oxa-1-azaspiro[4.4]nonane

HRID 276696Notes

Reaction equation

HRID 276696 reaction equation
O=S(Cl)Cl.[CH:5]1([NH:9][C:10]2([CH2:15]Cl)[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:8][CH2:7][CH2:6]1.ClCCN.[CH3:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[N:31]=[C:32]=[O:33]>>[CH:5]1([N:9]2[C:10]3([CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:15][O:33][C:32]2=[N:31][C:23]2[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:22]=2[CH3:21])[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 133692-ChloroethylamineHCID 24386Thionyl ChlorideHCID 42964562-Methyl-4-nitrophenyl isocyanateHCID 183165291-(Cyclobutylamino)-1-(chloromethyl)cyclopentane

Product 1

HCID 183164981-Cyclobutyl-2-(2-methyl-4-nitrophenylimino)-3-oxa-1-azaspiro[4.4]nonane

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 2-hydroxyethylamine was reacted with cyclobutanone according to Method B4a, Step 1 to give 5-aza-12-oxadispiro[3.1.4.2]dodecane. The oxazolidine was reduced according to Method B4a, Step 2 to give 1-(cyclobutylamino)-1-(hydroxymethyl)cyclopentane. The substituted 2-hydroxyethylamine was reacted with SOCl2 according to Method B7b to 1-(cyclobutylamino)-1-(chloromethyl)cyclopentane. The 2-chloroethylamine was reacted with 2-methyl-4-nitrophenyl isocyanate according to Method C4a to afford 1-cyclobutyl-2-(2-methyl-4-nitrophenylimino)-3-oxa-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-04d3696ce4a0422ca61cdbd8f7c678cc
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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