Cyanogen Bromide → HCID 69037480, compound

HRID 1985736Notes

Reaction equation

HRID 1985736 reaction equation
Cl.[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][C:10]([NH2:16])([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]1)=[O:6])[CH3:3].C[O-].[Na+].[N:20]#[C:21][Br:22]>CO>[BrH:22].[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][C:10]2([NH:16][C:21]([NH2:20])=[N:15][CH2:14][CH2:13]2)[CH2:9][CH2:8]1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 10942334Sodium MethoxideHCID 69038784HCID 69038784, compound

Product 1

HCID 69037480HCID 69037480, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 15.65 g (54.33 mmol) of 4-amino-4-(2-amino-ethyl)-piperidine-1-carboxylic acid ethyl ester hydrochloride (2:1) in 108 ml of methanol was added 21.73 ml (114.09 mmol) of a solution of sodium methoxide in methanol (5.55 N). The mixture was stirred at room temperature for 2 h. The precipitate was filtered and the filtrate was evaporated. The crude was dissolved in 108 ml of water and 5.75 g (54.33 mmol) of cyanogen bromide was added portion wise. The resulting mixture was stirred at room temperature for 16 h, evaporated to dryness, dissolved in ethanol and evaporated to dryness to give 17.56 g of pure compound as a brown solid.

Workup

  1. filtrationThe precipitate was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe crude was dissolved in 108 ml of water
  4. stirringThe resulting mixture was stirred at room temperature for 16 h
  5. customevaporated to dryness
  6. dissolutiondissolved in ethanol
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-8a16d17136bf415c9e2572a42c8f6743
Source dataset
uspto-grants-2009_06
Patent number
US07547705B2

Reaction notes

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