Cyclobutylamine → HCID 18324820, compound

HRID 1250901Notes

Reaction equation

HRID 1250901 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])C1=S)[CH:2]=[CH2:3].[CH:19]1(N)CCC1>O>[Cl:16][C:15]1[C:10]([NH:6][CH2:7][CH2:8][CH2:9][NH:4][CH:1]2[CH2:2][CH2:3][CH2:19]2)=[C:11]([CH3:17])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 9925711HCID 9925711, compound

Product 1

HCID 18324820HCID 18324820, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the hydrobromide salt of Example 12, Step B (6.64 g) and cyclobutylamine (4.15 g) was heated at 90° C. for 1.5 hours. The cooled mixture was diluted with water and extracted with dichloromethane. The extracts were washed with 20% aqueous sodium chloride, dried over anhydrous potassium carbonate and evaporated to a brown oil, which was flash chromatographed on Merck-60 flash silica gel (eluant: hexane-EtOAc 1:1 to remove less polar impurities, followed by dichloromethane-methanol-ammonium hydroxide 95:5:0.1) to provide the title compound (3.08 g, 63.5%), which was used as such in the next step.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with 20% aqueous sodium chloride
  3. dry with materialdried over anhydrous potassium carbonate
  4. customevaporated to a brown oil, which
  5. customchromatographed on Merck-60 flash silica gel (eluant: hexane-EtOAc 1:1 to remove less polar impurities, followed by dichloromethane-methanol-ammonium hydroxide 95:5:0.1)

Sources & evidence

ORD record
ord-eb340e370abe401ea6feb69b3c357f2e
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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