Sodium Hydroxide → 1'-Carbamoyl-1-(2-nitrophenyl)spiro[indoline3,4'-piperidine]

HRID 1632867Notes

Reaction equation

[C:1]([N:3]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])[CH2:9]2)[CH2:5][CH2:4]1)#[N:2].[OH-:26].[Na+]>C(COC)OC.Cl>[C:1]([N:3]1[CH2:4][CH2:5][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])[CH2:9]2)[CH2:7][CH2:8]1)(=[O:26])[NH2:2]

Participants

Conditions

Temperature: 0 °C

Procedure

9.93 g of 1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine] of Example 37 in 150 ml glyme and 100 ml 6M aqueous hydrochloric acid is heated at reflux under nitrogen for 1.5 hours. The mixture is cooled to 0° C., made basic with 50% aqueous sodium hydroxide (40 ml) and concentrated. The residue is dissolved in hot chloroform, washed with saturated sodium chloride, dried over anhydrous magnesium sulfate and contrated to give a crude product. Recrystallization from hot dimethylsulfoxide-dioxane-ether affords 1'-carbamoyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine], mp 217.5°-219.0° C.

Workup

temperatureat reflux under nitrogen for 1.5 hours
concentrationconcentrated
dissolutionThe residue is dissolved in hot chloroform
washwashed with saturated sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customto give a crude product
customRecrystallization from hot dimethylsulfoxide-dioxane-ether

Sources & evidence

ORD record: ord-770c4bf44c4345afa216838f3802fa3b
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04477667

Reaction notes

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