4-Methylbenzoyl Chloride → HCID 12940204, compound

HRID 1659634Notes

Reaction equation

HRID 1659634 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.[C:20]1([CH3:29])[CH:25]=[CH:24][C:23]([C:26]([Cl:28])=[O:27])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.[OH-].[Na+]>[ClH:28].[CH3:17][O:16][C:14]1[C:13]([O:18][CH3:19])=[CH:12][C:9]2[CH:10]3[N:5]([CH2:6][CH2:7][C:8]=2[CH:15]=1)[CH2:4][CH2:3][CH:2]([NH:1][C:26](=[O:27])[C:23]1[CH:24]=[CH:25][C:20]([CH3:29])=[CH:21][CH:22]=1)[CH2:11]3

Participants

5

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940204HCID 12940204, compoundYield 22.6%

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 (9 g, 0.034 mole) in 300 ml of toluene and 75 ml of 20% NaOH was added dropwise p-toluoyl chloride (6 g, 0.035 mole). The mixture was stirred in the cold for 1 hour and allowed to come to room temperature. The solid was collected by filtration and the toluene layer concentrated in vacuo whereupon the solid and concentrate were combined and chromatographed over silica gel using ethyl acetate-methanol (4:1) as eluant. The major fraction (6.2 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol, methanol and ethyl acetate, isolated and twice recrystallized from methanol-ethyl acetate to yield 3.2 g of the desired product, m.p. (decomposed at 268°-70°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR21##

Workup

  1. customto come to room temperature
  2. filtrationThe solid was collected by filtration
  3. concentrationthe toluene layer concentrated in vacuo whereupon the solid
  4. concentrationconcentrate
  5. customchromatographed over silica gel
  6. additionThe major fraction (6.2 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol, methanol and ethyl acetate
  7. customisolated
  8. customtwice recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-ae491c0c20cf41838da81a442e7c8ac4
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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