4-Fluorobenzoyl chloride → HCID 12940220, compound

HRID 1659639Notes

Reaction equation

HRID 1659639 reaction equation
[NH2:1][CH:2]1[CH2:11][CH:10]2[N:5]([CH2:6][CH2:7][C:8]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=32)[CH2:4][CH2:3]1.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([Cl:27])=[O:26])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.[OH-].[Na+]>[ClH:27].[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:1][CH:2]2[CH2:11][CH:10]3[N:5]([CH2:6][CH2:7][C:8]4[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=43)[CH2:4][CH2:3]2)=[O:26])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940220HCID 12940220, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a cold mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine, (7 g, 0.026 mole) in 200 ml of toluene and 50 ml of 20% NaOH, was added dropwise 4.5 g of 4-fluorobenzoyl chloride. The mixture was stirred in the cold for 1 hour and at room temperature for 1 hour. The resulting solid product was collected and chromatographed over silica gel using ethyl acetate-methanol-chloroform (3:1:1) as eluant. The major fraction (5.0 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and ether, isolated by removal of the solvent and recrystallized from methanol-ether to yield 2.3 g of the desired product, m.p. (decomposed at 257°-8°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR29##

Workup

  1. waitat room temperature for 1 hour
  2. customThe resulting solid product was collected
  3. customchromatographed over silica gel
  4. customisolated by removal of the solvent
  5. customrecrystallized from methanol-ether

Sources & evidence

ORD record
ord-463273ea548649c1b6f5e82fdf18f42f
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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