Cycloheptanone → HCID 10425048, compound

HRID 1743845Notes

Reaction equation

HRID 1743845 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)[CH2:22][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(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[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:17]=23)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10400CycloheptanoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 222365887-chloro-4-methyl-3,4,5,6-tetrahydro-2H-benzo[e][1,4]diazocin-1-ylamine

Product 1

HCID 10425048HCID 10425048, compoundYield 34.1%

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 cycloheptanone (6.65 g, 59.3 mmole) followed by p-toluenesulfonic acid monohydrate (3.2 g, 16.8 mmol) 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 0.55 g of the title compound as a white solid, mp 132-134° C. MS (ESI) m/z 303 ([M+H]+).

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-e66aa590f1ac41ac9a580b40a4111d6e
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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