Dimethyl Sulfide → 5-Phenyl-1-(piperidin-4-yl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 1379991Notes

Reaction equation

HRID 1379991 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:15][CH2:14][C:13]2=[O:29])[CH2:8][CH2:7]1)=O)C.CSC.CS(O)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[C:23]1([C:16]2[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:12]([CH:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)[C:13](=[O:29])[CH2:14][N:15]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 1068Dimethyl SulfideHCID 6395Methanesulfonic AcidHCID 11430Potassium CarbonateHCID 13450726HCID 13450726, compound

Product 1

HCID 133362855-Phenyl-1-(piperidin-4-yl)-1,3-dihydro-2H-1,4-benzodiazepin-2-oneYield 90%

Conditions

Temperature
70 °C

Procedure

A mixture of 100 mg (0.26 mmol) of the above product 12, 0.5 ml of methyl sulfide and 0.5 ml of methanesulfonic acid is heated at 70° C. for 5 hours. The reaction mixture is mixed with ice, basified with potassium carbonate and extracted with methylene chloride. The organic layer is washed with water, dried over anhydrous magnesium sulfate, and concentrated to give 73 mg of 1,3-dihydro-5-phenyl-1-(4-piperidinyl)-2H-1,4-benzodiazepin-2-one 13 as powders. The yield is 90%.

Workup

  1. additionThe reaction mixture is mixed with ice
  2. extractionextracted with methylene chloride
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-29212019790b4b73aec704143edc9a01
Source dataset
uspto-grants-1986_04
Patent number
US04579685

Reaction notes

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