Water → HCID 131714094, compound

HRID 615248Notes

Reaction equation

HRID 615248 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][C:10]3[C:15]([CH:6]2[CH2:5][NH:4][CH2:3]1)=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3.C(N(CC)CC)C.[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1.O>ClCCl>[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([N:4]2[CH2:3][C:2](=[O:1])[N:7]3[CH2:8][CH2:9][C:10]4[C:15]([CH:6]3[CH2:5]2)=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=4)=[O:33])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 15382915HCID 15382915, compound

Product 1

HCID 131714094HCID 131714094, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.62 g of (±)-4-oxo-9,10-dimethoxy-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline (I; R1 =H, R2 =R2 =OCH3) in 10 ml of dichloromethane was added 2 ml of triethylamine, and then 1.9 g of p-chlorobenzoyl chloride was slowly added 0°~5° C. The resultant mixture was stirred at 10° C. for 1.5 hours. To the reaction mixture was added water, and the organic layer was seperated. The organic extract was concentrated, and then the residue was triturated with ethyl acetate-ether to obtain 4.0 g (~100%) of the product, m.p. 139°~140° C.

Workup

  1. customwas slowly added 0°~5° C
  2. customthe organic layer was seperated
  3. extractionThe organic extract
  4. concentrationwas concentrated
  5. customthe residue was triturated with ethyl acetate-ether

Sources & evidence

ORD record
ord-7daad7892af648989b8531273602e8f8
Source dataset
uspto-grants-1985_02
Patent number
US04497952

Reaction notes

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