Chloride → 7-Phenylazepan-2-one

HRID 375279Notes

Reaction equation

HRID 375279 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[N:13]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=[O:28])=CC=1.[Cl-]>O>[C:1]1([CH:7]2[NH:13][C:8](=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 2758632-Phenylcyclohex-anone oxime

Product 1

HCID 105595527-Phenylazepan-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 ml round-bottomed flask equipped with N2 inlet were added 7.33 g (38.8 mmol) 2-phenylcyclohexanone oxime (Chem. Ber., 55, 3664 (1922)) and 25 ml pyridine. The solution was cooled to 0° C. and 9.61 g (50.4 mmol) p-toluenesulfonyl chloride was added. The reaction was allowed to stir overnight as the ice melted, and then poured into water. Excess chloride was skimmed off the surface, and the reaction mixture was stirred at pH 4 for 3 hours. The precipitate was filtered, washed with water, and dried to a solid, 4.65 g (55%), mp 135°-137° C. (J. Am. Chem. Soc., 82, 4671 (1960)gives mp 139°-141° C.).

Workup

  1. customTo a 250 ml round-bottomed flask equipped with N2 inlet
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried to a solid, 4.65 g (55%), mp 135°-137° C. (J. Am. Chem. Soc., 82, 4671 (1960)gives mp 139°-141° C.)

Sources & evidence

ORD record
ord-2d24431b4de14fe3becd0c082a404ee5
Source dataset
uspto-grants-1996_01
Patent number
US05484917

Reaction notes

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