4-Toluenesulfonyl chloride → 1-Benzyl-8-methoxy-4,5-dihydro-1H-benzo[C]azepin-3(2H)-one

HRID 625926Notes

Reaction equation

HRID 625926 reaction equation
C1(C)C=CC(S(Cl)(=O)=[O:8])=CC=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH2:28]([CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([O:45][CH3:46])[CH:43]=2)[CH2:38][CH2:37][C:36]1=[N:47]O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl>[CH2:28]([CH:35]1[C:44]2[CH:43]=[C:42]([O:45][CH3:46])[CH:41]=[CH:40][C:39]=2[CH2:38][CH2:37][C:36](=[O:8])[NH:47]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH2:28]([CH:35]1[C:44]2[CH:43]=[C:42]([O:45][CH3:46])[CH:41]=[CH:40][C:39]=2[CH2:38][CH2:37][NH:47][C:36]1=[O:8])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 86674675HCID 86674675, compound

Product 2

HCID 709822691-Benzyl-8-methoxy-4,5-dihydro-1H-benzo[C]azepin-3(2H)-oneYield 67%HCID 710870541-benzyl-8-methoxy-4,5-dihydro-1H-benzo[d]azepin-2(3H)-oneYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 8.46 mmol of p-toluenesulfonylchloride, 8.4 mmol triethylamine and 0.16 mmol of dimethylaminopyridine in 5 ml of dichloromethane was added a solution of 945 mg of 1-benzyl-7-methoxy-3,4-dihydronaphthalen-2(1H)-one oxime in 5 ml dichloromethane. The solution was stirred at room temperature over night. The mixture was diluted with dichloromethane and washed with water and saturated NaHCO3 solution. The combined organic layers were dried over MgSO4 and filtered. Evaporation of the solvent gave 1.9 g of crude material that was purified by flash chromatography to yield 637 mg of the desired isomer 1-benzyl-8-methoxy-4,5-dihydro-1H-benzo[c]azepin-3(2H)-one (67%) and 248 mg of its regioisomer 1-benzyl-8-methoxy-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one (26%).

Workup

  1. washwashed with water and saturated NaHCO3 solution
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customEvaporation of the solvent
  5. customgave 1.9 g of crude material that
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-7112cf6e84e1409f9abc57fda04ff649
Source dataset
uspto-grants-2016_04
Patent number
US09309200B2

Reaction notes

Loading…