Hydrazine hydrate (1:1) → alpha-(5-Aminopentyl)-alpha-(cyclohexylthio)-3,4-dimethoxy benzeneacetonitrile

HRID 863903Notes

Reaction equation

HRID 863903 reaction equation
[CH:1]1([S:7][C:8]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>>[NH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]([S:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)[C:9]#[N:10]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10505769a-(Cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-1,3-dioxo-2H-isoindole-2-heptanenitrile

Product 1

HCID 10667266alpha-(5-Aminopentyl)-alpha-(cyclohexylthio)-3,4-dimethoxy benzeneacetonitrileYield 88.8%

Procedure

The procedure of Example 25 is repeated using 2.0 g of α-(cyclohexylthio)-α-(3,4-dimethoxyphenyl)-1,3-dioxo-2H-isoindole-2-heptanenitrile and 3.0 mL of hydrazine hydrate. This affords 1.32 g of the desired product as a light yellow oil. Calcd for C21H32N2SO2 0.7M H2O: C=64.81, H=8.81, N=7.20, S=8.24 Found C=65.04, H=8.49, N=6.98, S=8.20

Sources & evidence

ORD record
ord-cf29ca37abc24b00ba2e734ff9988dd9
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

Loading…