Ammonia → 2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-1-(1-methyl-4-piperidinyl)-5-phenyl-

HRID 1379989Notes

Reaction equation

HRID 1379989 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15](=[N:22][CH2:23][C:24]([O:26]CC)=O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:4][CH2:3]1.N>FC(F)(F)C(O)=O>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:22][CH2:23][C:24]2=[O:26])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13450681HCID 13450681, compound

Product 1

HCID 566582H-1,4-Benzodiazepin-2-one, 1,3-dihydro-1-(1-methyl-4-piperidinyl)-5-phenyl-Yield 87%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 379 mg of the above product 2 in 4 ml of trifluoroacetic acid is refluxed under heating for 16 hours. The reaction mixture is mixed with ice water, basified with ammonia and extracted with methylene chloride. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue is crystallized from ether-petroleum ether to give 278 mg of 1-(1-methyl-4-piperidinyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one 3 as crystals melting at 158°-159° C. The yield is 87%.

Workup

  1. temperatureunder heating for 16 hours
  2. extractionextracted with methylene chloride
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is crystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-8f6f87765e7343b0a7798fe1afcc5e65
Source dataset
uspto-grants-1986_04
Patent number
US04579685

Reaction notes

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