Cyclopentanone → HCID 10446058, compound

HRID 1743875Notes

Reaction equation

HRID 1743875 reaction equation
[Cl: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(Cl)Cl>[Cl: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 22236586HCID 22236586, compound

Product 1

HCID 10446058HCID 10446058, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-chloro-4-methyl-3,4,5,6-tetrahydro-2H-benzo[e][1,4]diazocin-1-ylamine (3.5 g, 15.5 mmole) in 1-propanol (200 mL) was added cyclopentanone (20.0 ml, 226.1 mmole), followed by p-toluenesulfonic acid monohydrate (11.0 g, 57.8 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 methylene chloride (300 mL) and washed with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous sodium chloride (200 mL), dried (sodium sulfate) and concentrated in vacuo. Purification by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1) provided 1.3 g of the title compound. 0.11 g of the free amine was treated with one equivalent of fumaric acid in ethanol to form a fumarate salt (0.12 g, mp 209-211° C.). MS (ES) m/z 275.1 ([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 (200 mL), saturated aqueous sodium chloride (200 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-71062cacc03a45ec9defcd6290c369b3
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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