Methyl Bromide → HCID 10071284, compound

HRID 1724672Notes

Reaction equation

HRID 1724672 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1([OH:25])[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:11])[CH2:2]2.[CH3:26][Br:27]>C(#N)C.C(Cl)(Cl)Cl>[Br-:27].[OH:25][C:12]1([C:10]([NH:9][CH:3]2[CH:4]3[CH2:5][CH2:6][N+:1]([CH3:26])([CH2:8][CH2:7]3)[CH2:2]2)=[O:11])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:19]2[C:24]1=[CH:23][CH:22]=[CH:21][CH:20]=2

Participants

5

Reactant 2

HCID 6323Methyl BromideHCID 10359531HCID 10359531, compound

Product 1

HCID 10071284HCID 10071284, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent2×

Procedure

0.245 g (0.00073 mol) of N-(1-azabicyclo[2.2.2]oct-3-yl)-9-hydroxy-9H-fluorene-9-carboxamide (Example 41) were dissolved in 4 ml of acetonitrile and 6 ml of CHCl3. To this solution 5.46 ml of a 1 M solution of methyl bromide in acetonitrile were added and the mixture was stirred for 96 h at room temperature under N2 atmosphere. After this time the solvents were evaporated. The residue was coevaporated with ether three times. Ether was added to the residue and the mixture stirred. The solid obtained was filtered and washed several times with ether. The yield was 0.26 g (83.8%) of the title compound.

Workup

  1. customAfter this time the solvents were evaporated
  2. additionEther was added to the residue
  3. stirringthe mixture stirred
  4. customThe solid obtained
  5. filtrationwas filtered
  6. washwashed several times with ether

Sources & evidence

ORD record
ord-29d32397520941cdb07eefea09e6293a
Source dataset
uspto-grants-2009_02
Patent number
US07488735B2

Reaction notes

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