Cyclohexanone → HCID 10356798, compound

HRID 1743876Notes

Reaction equation

HRID 1743876 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)[CH2:21][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[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=13

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 22236586HCID 22236586, compound

Product 1

HCID 10356798HCID 10356798, compoundYield 48%

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 (4.9 g, 22.0 mmole) in 1-propanol (300 mL) was added cyclohexanone (25.0 ml, 240.0 mmole), followed by p-toluenesulfonic acid monohydrate (10.0 g, 50.0 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 3.05 g of the title compound. 0.335 g of the free amine was treated with one equivalent of fumaric acid in ethanol to form a fumarate salt (0.544 g, mp 212-214° C.). MS (ES) m/z 289 ([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-b58518e6b63e4a1c943bad953fcd1106
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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