Thiomorpholine → HCID 9916982, compound

HRID 1420521Notes

Reaction equation

HRID 1420521 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:16]([CH:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:26])[CH2:24]Cl)[CH2:19][CH2:18]3)[C:10]3=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[C:27]=1[Br:28].[NH:29]1[CH2:34][CH2:33][S:32][CH2:31][CH2:30]1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:16]([CH:17]3[CH2:18][CH2:19][N:20]([C:23](=[O:26])[CH2:24][N:29]4[CH2:34][CH2:33][S:32][CH2:31][CH2:30]4)[CH2:21][CH2:22]3)[C:10]3=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[C:27]=1[Br:28]

Participants

5

Reactant 2

HCID 67164ThiomorpholineHCID 18782110HCID 18782110, compound

Product 1

HCID 9916982HCID 9916982, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ~0.11 g of 4-[8-Chloro-3,7-dibromo-5,6-dihydro-11H-benzo[5,6 ]cyclohepta[1,2-b]pyridin-11-yl]-1-(chloroacetyl)piperidine in 5 ml of CH2Cl2 is added 0.12 ml of thiomorpholine and the mixture is stirred at ambient temperature for 24 h, and diluted with 20 ml of distilled water. The layers are separated and the aqueous layer is back extracted with 10 ml of CH2Cl2. The combined organic layer is washed once with saturated brine, dried over Mg2SO4, filtered and evaporated to a brown residue. Flash chromatography over 20 g silica gel with 200 ml of 3% MeOH/CH2Cl2 gives 0.12 g of the title compound, yield in two steps is 93.8%. MS: 614.5 (M+H).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous layer is back extracted with 10 ml of CH2Cl2
  3. washThe combined organic layer is washed once with saturated brine
  4. dry with materialdried over Mg2SO4
  5. filtrationfiltered
  6. customevaporated to a brown residue

Sources & evidence

ORD record
ord-fbd18b981bc34757b525ac74cc6a8bc4
Source dataset
uspto-grants-2000_06
Patent number
US06071907

Reaction notes

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