Ethylenediamine → HCID 18623231, compound

HRID 1860425Notes

Reaction equation

HRID 1860425 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][NH:9][C:8](=O)[CH2:7]1)=[O:5].[BH4-].[Na+].[CH2:20]([NH2:23])[CH2:21][NH2:22]>C1C=CC=CC=1>[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([NH:22][CH2:21][CH2:20][NH2:23])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 18623232HCID 18623232, compound

Product 1

HCID 18623231HCID 18623231, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-(2,4-difluorobenzoyl)piperidinone (1.50 g, 6.27 mmol) in benzene (40 mL) and ethylenediamine (4.0 mL) was refluxed for 6 hours. The resulting mixture was concentrated to a residue which was dissolved in MeOH (30 mL). The mixture was cooled (0° C.) and NaBH4 (1.0 g, 26.4 mmol) was slowly added. After stirred for an hour, the mixture was concentrated and quenched with 1 N NaOH (50 mL). The mixture was extracted with CH2Cl2 (5×20 mL), dried (K2CO3), and was concentrated. The residue was purified by flash chromatography (CHCl3—MeOH—2 M NH3 in MeOH 100:10:2 to 100:20:5) to afford the product as an pale yellow solid (670 mg, 38%).

Workup

  1. concentrationThe resulting mixture was concentrated to a residue which
  2. dissolutionwas dissolved in MeOH (30 mL)
  3. additionwas slowly added
  4. concentrationthe mixture was concentrated
  5. customquenched with 1 N NaOH (50 mL)
  6. extractionThe mixture was extracted with CH2Cl2 (5×20 mL)
  7. dry with materialdried (K2CO3)
  8. concentrationwas concentrated
  9. customThe residue was purified by flash chromatography (CHCl3—MeOH—2 M NH3 in MeOH 100:10:2 to 100:20:5)

Sources & evidence

ORD record
ord-717dafdd0c514ad49a4c65e0cddce34d
Source dataset
uspto-grants-2003_03
Patent number
US06531471B2

Reaction notes

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