Hydrochloric Acid → HCID 68445055, compound

HRID 2233173Notes

Reaction equation

HRID 2233173 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6](=[O:12])[N:5]3[CH2:13][CH:14]([CH2:15][N:16]4[CH2:21][CH2:20][CH:19]([NH:22]C(=O)OC(C)(C)C)[CH2:18][CH2:17]4)[C:3]=1[C:4]=23.Cl>ClCCl.CO.O.O1CCOCC1>[NH2:22][CH:19]1[CH2:18][CH2:17][N:16]([CH2:15][CH:14]2[C:3]3[C:4]4[N:5]([C:6](=[O:12])[CH:7]=[N:8][C:9]=4[CH:10]=[CH:11][C:2]=3[F:1])[CH2:13]2)[CH2:21][CH2:20]1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 86628361HCID 86628361, compound

Product 1

HCID 68445055HCID 68445055, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl {1-[(7-fluoro-3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]quinoxalin-6-yl)methyl]-4-piperidinyl}carbamate (8.13 g, 20.2 mmol) in dichloromethane (150 ml) and methanol (100 ml) was cooled in iced water. Hydrogen chloride in 1,4-dioxane (4M, 160 ml) was added gradually, then the mixture was stirred for 1.5 h. The mixture was evaporated and the residue was triturated with ether and filtered off. The solid was partially dissolved in 25% methanol/dichloromethane (200 ml) and stirred with MP-carbonate (3.03 mmol/g, 27 g) for 1 h. The resin was filtered off, washed a few times with 10% methanol/dichloromethane and methanol alternately, and the filtrate was evaporated to give the product (5.96 g, 98%).

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated with ether
  3. filtrationfiltered off
  4. dissolutionThe solid was partially dissolved in 25% methanol/dichloromethane (200 ml)
  5. stirringstirred with MP-carbonate (3.03 mmol/g, 27 g) for 1 h
  6. filtrationThe resin was filtered off
  7. washwashed a few times with 10% methanol/dichloromethane and methanol alternately
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d9413c2dc2be4be0b44d57d2f69da04b
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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