Cyclopentanone → HCID 10422650, compound

HRID 1743860Notes

Reaction equation

HRID 1743860 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8][N:7](N)[C:6]=2[CH:15]=1.[C:16]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CC.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8][N:7]3[C:6]=2[C:15]=1[C:16]1[CH2:20][CH2:19][CH2:18][C:17]=13

Participants

6

Reactant 3

HCID 8452CyclopentanoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 22236593HCID 22236593, compound

Product 1

HCID 10422650HCID 10422650, compoundYield 20.3%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 9-fluoro-4-methyl-3,4,5,6-tetrahydro-2H-benzo[e][1,4]diazocin-1-ylamine (4.0 g, 19.1 mmole) in 1-propanol (300 mL) was added cyclopentanone (14.3 ml, 169.6 mmole), followed by p-toluenesulfonic acid monohydrate (10.3 g, 53.3 mmole), and the resulting reaction mixture was refluxed for 30 hours. The reaction mixture was cooled to room temperature and solvent removed in vacuo to produce a brown residue. The residue was diluted with ethyl acetate (500 mL) and washed with saturated aqueous sodium bicarbonate (350 mL), saturated aqueous sodium chloride (350 mL), dried (sodium sulfate) and concentrated in vacuo. Purification by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1) provided 1.0 g of the title compound. 70.5 mg of the free amine was treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 168-170° C. MS (ES) m/z 259.12 ([M+H]+).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 30 hours
  3. customsolvent removed in vacuo
  4. customto produce a brown residue
  5. washwashed with saturated aqueous sodium bicarbonate (350 mL), saturated aqueous sodium chloride (350 mL)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customPurification by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1)

Sources & evidence

ORD record
ord-94086ad3265f48fb8a9cf9c9ebd9bf03
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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