Toluene → 2-(Benzylamino)-3,4,5,6-tetrahydrobenzamide

HRID 610611Notes

Reaction equation

HRID 610611 reaction equation
[CH2:1]1[CH2:7][CH:6]([C:8]([NH2:10])=[O:9])[C:4](=O)[CH2:3][CH2:2]1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC=CC=1>O>[CH2:11]([NH:18][C:4]1[CH2:3][CH2:2][CH2:1][CH2:7][C:6]=1[C:8]([NH2:10])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7504BenzylamineHCID 5879892-Oxocyclohexanecarboxamide

Product 1

HCID 106571002-(Benzylamino)-3,4,5,6-tetrahydrobenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of cyclohexanone-2-carboxamide (U.S. Pat. No. 4,169,952 to du Pont de Nemours, (1979)) (10.0 g), benzylamine (8.4 g), toluene (35 mL) and molecular sieves (Union Carbide 3A, 2 g) was refluxed for 2 h in a Dean-Stark water separator. The reaction mixture was filtered, and the filtrate was evaporated. The residue was crystallized from light petroleum to give the title compound (16 g). Mp 73-74° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from light petroleum

Sources & evidence

ORD record
ord-f1f1d95b92ca4594bd5486d982f41276
Source dataset
uspto-grants-1999_12
Patent number
US05998613

Reaction notes

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