Water → HCID 57803050, compound

HRID 2102676Notes

Reaction equation

HRID 2102676 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].N1CCCCC1.O>CC(O)C>[C:15]([O:14][C:12]([N:19]1[CH2:24][CH2:23][C:22](=[C:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[CH2:21][CH2:20]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 57803050HCID 57803050, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 6-chlorooxindole (1.68 g, 10 mmol) (Cresent Chem.), 1-BOC-4-piperidone (2.20 g, 11.0 mmol) (Fluka), and piperidine (85 mg, 1 mmol) (Aldrich) in 2-propanol (30 mL) was heated at 100° C. for 2 days. Hot water (30 mL) was added to the hot reaction mixture and mixture allowed to cool to room temperature. After standing in refrigerator for 2 hours, crystalline material was collected and washed with cold aqueous methanol to give 4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-piperidine-1-carboxylic acid tert-butyl ester as a yellow crystalline material. (Yield 2.88 g, 82.4%).

Workup

  1. temperatureto cool to room temperature
  2. customcrystalline material was collected
  3. washwashed with cold aqueous methanol

Sources & evidence

ORD record
ord-8c7d6025262f47b9b92d7cbd6529a9c6
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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