Dimethylformamide → HCID 11500672, compound

HRID 2356976Notes

Reaction equation

HRID 2356976 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]([CH2:20][C:21]#[N:22])[CH2:15][CH2:16][O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C>C1COCC1>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]([CH2:20][CH2:21][NH2:22])[CH2:15][CH2:16][O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 58668697HCID 58668697, compound

Product 1

HCID 11500672HCID 11500672, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(7-Benzenesulfonyl-chroman-4-yl)-acetonitrile (397 mg, 1.26 mmol) was dissolved in 5 mL THF, and 190 ul (1.9 mmol) of BH3.DMF was added. The reaction mixture was heated to reflux for one hour and then cooled to room temperature, quenched by addition of methanol, and diluted with water. The aqueous mixture was extrated with EtOAc. The organic phase was dried over MgSO4, and solvent was removed under reduced pressure. The residue was chromatographed through silica gel (MeOH:CH2Cl2:NH4OH 8%:90%:2%), and solvent was removed under reduced pressure to yield 120 mg (0.38 mmol, 30%) of 2-(7-benzenesulfonyl-chroman-4-yl)-ethylamine. This product was dissolved in 2N HCl/EtOH and recrystallized by addition of Et2O to afford 95 mg of the corresponding hydrochloride salt. Mp: 244.6-245.8° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for one hour
  3. customquenched by addition of methanol
  4. additiondiluted with water
  5. dry with materialThe organic phase was dried over MgSO4, and solvent
  6. customwas removed under reduced pressure
  7. customThe residue was chromatographed through silica gel (MeOH:CH2Cl2:NH4OH 8%:90%:2%), and solvent
  8. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-19abe09090c54ec3a144cae5f7929989
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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