Ammonia → 5'-Amino-1'-(3-aminopropyl)spiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one

HRID 853888Notes

Reaction equation

HRID 853888 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][C:15]#[N:16])[C:8](=[O:17])[C:7]12[O:22][CH2:21][CH2:20][CH2:19][O:18]1)([O-])=O.N.C1COCC1>[Ni].CCO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][CH2:15][NH2:16])[C:8](=[O:17])[C:7]12[O:22][CH2:21][CH2:20][CH2:19][O:18]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 589325573-(5'-Nitro-2'-oxospiro[1,3-dioxane-2,3'-indol]-1'(2'H)-yl)propanenitrile

Product 1

HCID 589325815'-Amino-1'-(3-aminopropyl)spiro[1,3-dioxane-2,3'-indol]-2'(1'H)-oneYield 73%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(5′-nitro-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′(2′H) -yl)propanenitrile (2.12 g, 7.76 mmol) and wet Raney Nickel (2.29 g) in 2M EtOH.NH3 (95 mL) and THF (35 mL) was hydrogenated in a Parr Hydrogenation Bottle at 50 lb/in2 H2 for 17 hr. The Raney Nickel was removed by filtration through Celite and the filtrate was concentrated. The crude product was purified on Biotage KP silica gel eluting with a step gradient of CH2Cl2/CH3OH/NH4OH (95/3/2) to (85/10/5) to give the title compound as a yellow foam (1.57 g, 73% yield). NMR (300 Mz, DMSO-d6): consistent

Workup

  1. customfor 17 hr
  2. customThe Raney Nickel was removed by filtration through Celite
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified on Biotage KP silica gel eluting with a step gradient of CH2Cl2/CH3OH/NH4OH (95/3/2) to (85/10/5)

Sources & evidence

ORD record
ord-78dde1dacef547479ec0bf5c89690f53
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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