Sodium Hydroxide → HCID 57833617, compound

HRID 730075Notes

Reaction equation

HRID 730075 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[C:16]1[C:29]3[CH:28]=[CH:27][CH:26]=[C:25]([NH2:30])[C:24]=3[O:23][C:22]3[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S-:31][C:32]#[N:33].[K+].BrBr.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[C:16]1[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:23][C:24]3[C:29]1=[CH:28][CH:27]=[C:26]1[S:31][C:32]([NH2:33])=[N:30][C:25]1=3)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 516872Potassium thiocyanateHCID 57833608HCID 57833608, compound

Product 1

HCID 57833617HCID 57833617, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 9-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-9H-xanthen-4-ylamine in glacial acetic acid (0.1 to 1 M solution) may be added potassium thiocyanate (2 equiv). A solution of bromine (1 equiv) in glacial acetic acid (0.5 to 2 M solution) may be added slowly, and the resulting mixture may be stirred at rt for 1 to 4 hr. The solution may be basified with a sodium hydroxide solution (5 to 20%), and extracted with a suitable organic solvent such as ethyl acetate. The organic layer may be separated, dried over sodium sulfate, filtered, and evaporated. The residue may be purified via column chromatography to yield Compound 1h.

Workup

  1. extractionextracted with a suitable organic solvent such as ethyl acetate
  2. customThe organic layer may be separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue may be purified via column chromatography
  7. customto yield Compound 1h.

Sources & evidence

ORD record
ord-14fb1dcc8a1746f4bef0277ac4f82e5b
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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