2-Aminobenzonitrile → HCID 21699658, compound

HRID 1597279Notes

Reaction equation

HRID 1597279 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[NH2:19][C:18]1[C:12]2[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10][C:11]=2[N:15]=[C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=12

Participants

5

Reactant 2

HCID 729132-AminobenzonitrileHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 21699658HCID 21699658, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

1-t-Butoxycarbonyl-4-piperidone (1.69 g, 8.46 mmol), zinc chloride (1.50 g, 11.0 mmol) and 2-aminobenzonitrile (1.0 g, 8.46 mmol) were mixed and then reacted at 90° C. for 1 hour. The reaction mixture was cooled to room temperature to obtain a solid, which was ground together with toluene and filtered. The thus treated solid was suspended in chloroform and concentrated aqueous ammonia was added thereto and stirred. The chloroform layer was separated, dried over anhydrous sodium sulfate and then concentrated to obtain the desired compound (0.54 g, 1.8 mmol, 21%).

Workup

  1. customreacted at 90° C. for 1 hour
  2. customto obtain a solid, which
  3. filtrationfiltered
  4. additionconcentrated aqueous ammonia was added
  5. customThe chloroform layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-803ca7925fc14753847a5d3bdf53babc
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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