Benzoyl chloride, 3,4,5-trimethoxy- → HCID 12940202, compound

HRID 1659633Notes

Reaction equation

HRID 1659633 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([Cl:8])=[O:7].[NH2:16][CH:17]1[CH2:26][CH:25]2[N:20]([CH2:21][CH2:22][C:23]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:24]=32)[CH2:19][CH2:18]1>N1C=CC=CC=1>[ClH:8].[CH3:32][O:31][C:29]1[C:28]([O:33][CH3:34])=[CH:27][C:24]2[CH:25]3[N:20]([CH2:21][CH2:22][C:23]=2[CH:30]=1)[CH2:19][CH2:18][CH:17]([NH:16][C:6](=[O:7])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=1)[CH2:26]3

Participants

4

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 13074442HCID 13074442, compound

Product 1

HCID 12940202HCID 12940202, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 3,4,5-trimethoxy benzoyl chloride (13 g) in pyridine was added dropwise to 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (13 g) in 200 ml of pyridine, and the solution was warmed at 60°-70° for 30 minutes and poured into ice water. The mixture was extracted with chloroform and the extracts dried over MgSO4, concentrated in vacuo and the concentrated material chromatographed over silica gel using ethyl acetate-methanol-chloroform (4:1:0.5) as eluant. The major fraction (9.9 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol, methanol and ethyl acetate, isolated as a solid and recrystallized from methanol-ethyl acetate and again from methanol to yield 3.6 g of the desired product, m.p. (decomposed at 259°-61°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR20##

Workup

  1. temperaturethe solution was warmed at 60°-70° for 30 minutes
  2. extractionThe mixture was extracted with chloroform
  3. dry with materialthe extracts dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customthe concentrated material chromatographed over silica gel
  6. additionThe major fraction (9.9 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol, methanol and ethyl acetate
  7. customisolated as a solid
  8. customrecrystallized from methanol-ethyl acetate and again from methanol

Sources & evidence

ORD record
ord-37ece01472f34d29a54e8b0b3db7ac30
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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