Cyclopentanone → HCID 10061933, compound

HRID 1743843Notes

Reaction equation

HRID 1743843 reaction equation
[Cl:1][C:2]1[C:13]2[CH2:12][CH2:11][N:10]([CH3:14])[CH2:9][CH2:8][N:7](N)[C:6]=2[CH:5]=[CH:4][CH:3]=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>[Cl:1][C:2]1[C:13]2[CH2:12][CH2:11][N:10]([CH3:14])[CH2:9][CH2:8][N:7]3[C:6]=2[C:5]([C:16]2[CH2:20][CH2:19][CH2:18][C:17]=23)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8452CyclopentanoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 222365887-chloro-4-methyl-3,4,5,6-tetrahydro-2H-benzo[e][1,4]diazocin-1-ylamine

Product 1

HCID 10061933HCID 10061933, compoundYield 13.7%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-chloro-4-methyl-3,4,5,6-tetrahydro-2H-benzo[e][1,4]diazocin-1-ylamine (1.20 g, 5.32 mmole) in 1-propanol (100 mL) was added cyclopentanone (6.66 g, 79.14 mmole) followed by p-toluenesulfonic acid monohydrate (3.2 g, 16.8 mmole) and the resulting reaction mixture was refluxed for 24 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 (300 mL) and washed with saturated sodium bicarbonate (150 mL), saturated sodium chloride (150 mL), dried (sodium sulfate) and concentrated. Purification by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1) provided 0.20 g of the title compound as a white solid, mp 138-140° C.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 24 hours
  3. customsolvent removed in vacuo
  4. customto produce a brown residue
  5. washwashed with saturated sodium bicarbonate (150 mL), saturated sodium chloride (150 mL)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1)

Sources & evidence

ORD record
ord-7af8f884fbe14f11963d1621ae1e846f
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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