Ethyl Acetate → 5,10-Dihydro-5-{[(1-methyl-4-piperidinyl)oxy]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 325883Notes

Reaction equation

HRID 325883 reaction equation
Cl[C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]1=2)=[O:3].[CH3:20][N:21]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]1.C(OCC)(=O)C>ClC1C=CC=CC=1>[CH3:20][N:21]1[CH2:26][CH2:25][CH:24]([O:27][C:2]([N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[NH:7][C:6]3[CH:16]=[CH:17][CH:18]=[CH:19][C:5]2=3)=[O:3])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 660484-Piperidinol, 1-methyl-HCID 132767455-chlorocarbonyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

Product 1

HCID 132767485,10-Dihydro-5-{[(1-methyl-4-piperidinyl)oxy]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A quantity of 4.1 gm (0.015 mol) of 5-chlorocarbonyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one was refluxed with 3.45 gm (0.03 mol) of 1-methyl-4-piperidinol in 50 ml of chlorobenzene for two hours. After cooling, the reaction solution was diluted by the addition of 200 ml of ethyl acetate and then extracted exhaustively with 15% hydrochloric acid. The combined extracts were neutralized with potassium carbonate and extracted several times with chloroform, and the combined chloroform extracts were evaporated to dryness in vacuo. By recrystallization from ethyl acetate, colorless crystals were obtained, m.p.: 203°-204° C. Yield: 1.2 gm (23% of theory).

Workup

  1. temperatureAfter cooling
  2. extractionextracted exhaustively with 15% hydrochloric acid
  3. extractionextracted several times with chloroform
  4. customthe combined chloroform extracts were evaporated to dryness in vacuo
  5. customBy recrystallization from ethyl acetate
  6. customcolorless crystals were obtained

Sources & evidence

ORD record
ord-4c46a65b05b74d629f7671bba4c04a33
Source dataset
uspto-grants-1984_04
Patent number
US04443452

Reaction notes

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