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

HRID 67225Notes

Reaction equation

HRID 67225 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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 128016151'-Cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

Product 1

HCID 128016451'-Carbamoyl-1-(2-nitrophenyl)spiro[indoline3,4'-piperidine]

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 80711,2-DimethoxyethaneSolvent

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 6 M 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

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

Sources & evidence

ORD record
ord-4a119235bd9849c89317927716eada23
Source dataset
uspto-grants-1982_08
Patent number
US04345081

Reaction notes

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