p-Anisoyl chloride → HCID 20559725, compound

HRID 1659640Notes

Reaction equation

HRID 1659640 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]4[O:16][CH2:17][O:18][C:13]4=[CH:12][C:9]=32)[CH2:4][CH2:3]1.[OH-].[Na+].[C:21]([Cl:31])(=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[ClH:31].[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([NH:1][CH:2]2[CH2:11][CH:10]3[N:5]([CH2:6][CH2:7][C:8]4[CH:15]=[C:14]5[O:16][CH2:17][O:18][C:13]5=[CH:12][C:9]=43)[CH2:4][CH2:3]2)=[O:30])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 14798Sodium HydroxideHCID 20559728HCID 20559728, compound

Product 1

HCID 20559725HCID 20559725, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-methylenedioxy-2H-benzo[a]quinolizine (6.5 g, 0.026 mole), 20% NaOH (50 ml) and 200 ml of toluene was cooled in an ice bath and p-anisoyl chloride (4.6 g) was added dropwise. The mixture was stirred in the cold for one hour whereupon the solid was collected and recrystallized from aqueous methanol-DMF. The free base was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol and ethyl acetate. The resulting solid was collected and twice recrystallized from methanol-ethyl acetate to yield 3.3 g of the desired product, m.p. (decomposed at 228°-30°). This product conforms to Formula II where R1 and R2 combined are ##STR34## R3 is H and R4 is ##STR35##

Workup

  1. temperaturewas cooled in an ice bath
  2. customwas collected
  3. customrecrystallized from aqueous methanol-DMF
  4. additionThe free base was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol and ethyl acetate
  5. customThe resulting solid was collected
  6. customtwice recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-48a02eabd6da4b1a940bc8902db24e0b
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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