Toluene → HCID 70592562, compound

HRID 224615Notes

Reaction equation

HRID 224615 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:22])[C:14]2=[O:23])[CH2:10][CH2:9]1)C1C=CC=CC=1.[CH2:24]([O:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(C)C=CC=CC=1>O>[CH2:24]([O:31][C:32]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:22])[C:14]2=[O:23])[CH2:10][CH2:9]1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 10387Benzyl chloroformateHCID 59433461HCID 59433461, compound

Product 1

HCID 70592562HCID 70592562, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15.1 g of 1'-benzyl-1-methyl-2-oxoindoline-3-spiro-4'-piperidine, 33.5 g of benzyloxycarbonyl chloride and 530 ml of toluene was refluxed for 6 hours. The resulting mixture was poured into water and extracted with ethylacetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Thus obtained oil was washed with n-hexane to give 1'-benzyloxycarbonyl-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine.

Workup

  1. temperaturewas refluxed for 6 hours
  2. extractionextracted with ethylacetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. washThus obtained oil was washed with n-hexane

Sources & evidence

ORD record
ord-5176224f4cf448769acba6134a9f7059
Source dataset
uspto-grants-1980_11
Patent number
US04233307

Reaction notes

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