Potassium Carbonate → 5-{3-[4-(4-Fluorobenzoyl)piperidinyl]propyl}-10,11-dihydro5H-dibenz[b,f]azepine

HRID 917946Notes

Reaction equation

HRID 917946 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[F:20][C:21]1[CH:34]=[CH:33][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O.O.C(O)(=O)C(O)=O>C(O)(C)C.CN(C)C=O>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][N:5]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[CH2:9][CH2:8][C:7]4[CH:16]=[CH:17][CH:18]=[CH:19][C:6]3=4)[CH2:29][CH2:28]2)=[O:26])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 61373Oxalic acid dihydrateHCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepineHCID 27244404-(4-Fluorobenzoyl)piperidine

Product 1

HCID 215244585-{3-[4-(4-Fluorobenzoyl)piperidinyl]propyl}-10,11-dihydro5H-dibenz[b,f]azepineYield 32%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture containing 4.5 gms. (0.017 mole) of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine, 3.4 gms (0.017 mole) of 4-(4-fluorobenzoyl)piperidine, 10.0 gms. of potassium carbonate and 75 ml. of dimethylformamide was heated at 90°-100°C. for 16 hours. The cooled suspension was filtered, the solvent removed at reduced pressure and the residual oil was taken up in ether and filtered to remove insoluble materials. The clear filtrate was treated with a solution of 2.1 gms. (0.017 mole) of oxalic acid dihydrate in isopropanol. The oxalate which separated on cooling was collected by filtration. The salt melted at 150°-155°C. and weighed 2.9 gms. (32% yield). After recrystallization from isopropanol the salt melted at 156°-159°C.

Workup

  1. additionA stirred mixture containing 4.5 gms
  2. filtrationThe cooled suspension was filtered
  3. customthe solvent removed at reduced pressure
  4. filtrationfiltered
  5. customto remove insoluble materials
  6. additionThe clear filtrate was treated with a solution of 2.1 gms
  7. customThe oxalate which separated
  8. temperatureon cooling
  9. filtrationwas collected by filtration
  10. customAfter recrystallization from isopropanol the salt melted at 156°-159°C.

Sources & evidence

ORD record
ord-eefecd4953624684b875d6b9317312d7
Source dataset
uspto-grants-1976_07
Patent number
US03968217

Reaction notes

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