Allylamine → HCID 68576883, compound

HRID 2390914Notes

Reaction equation

HRID 2390914 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8](O)[CH2:9][N:10]([CH2:17][CH2:18]O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:33]([NH2:36])[CH:34]=[CH2:35].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:17][CH2:18][N:36]2[CH2:33][CH:34]=[CH2:35])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 7853AllylamineHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68576987HCID 68576987, compound

Product 1

HCID 68576883HCID 68576883, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)(phenyl)amino]-1-ethanol (1.68 g, 4.94 mmol) produced in Example 11, ethyl acetate (10 mL) and triethylamine (1.75 g, 3.5 equivalents) were added. The mixture was cooled to 5° C. Methanesulfonyl chloride (1.81 g, 3.2 equivalents) was added dropwise thereto, and then allylamine (1.69 g, 6.0 equivalents) was added dropwise thereto. The mixture was stirred at 5° C. for 1 hour and then at 25° C. for 2 hours. The reaction mixture was transferred in an autoclave, and stirred at 50° C. for 18 hours. The mixture was cooled to room temperature, and then 10 wt % aqueous solution of sodium carbonate (8.38 g) was added to the mixture. After the organic layer and aqueous layer were separated, the organic layer was washed twice with distilled water (10 mL). The obtained organic layer was concentrated to give 1.11 g of a concentrate as yellow oil (chemical purity: 30.2 area %). The concentrate was purified by column chromatography (gel: silica gel, solvent: ethyl acetate/hexane=1/9), and the obtained fractions were concentrated and dried under vacuum, to obtain 307 mg of the title compound as colorless oil (yield: 19%, chemical purity: 98.1 area %). The retention time in the chemical purity analysis method was 56.6 min.

Workup

  1. waitat 25° C. for 2 hours
  2. stirringstirred at 50° C. for 18 hours
  3. temperatureThe mixture was cooled to room temperature
  4. customAfter the organic layer and aqueous layer were separated
  5. washthe organic layer was washed twice with distilled water (10 mL)
  6. concentrationThe obtained organic layer was concentrated
  7. customto give 1.11 g of
  8. concentrationa concentrate as yellow oil (chemical purity: 30.2 area %)
  9. customThe concentrate was purified by column chromatography (gel: silica gel, solvent: ethyl acetate/hexane=1/9)
  10. concentrationthe obtained fractions were concentrated
  11. customdried under vacuum

Sources & evidence

ORD record
ord-b647b25e62e64d869b0bb740b693a4fa
Source dataset
uspto-grants-2012_09
Patent number
US08273883B2

Reaction notes

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