Acetonitrile → HCID 18333003, compound

HRID 2269737Notes

Reaction equation

HRID 2269737 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(#N)C.[N:9]1([CH2:14][CH:15]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH2:16]2)[CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>O>[CH3:1][S:2]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:24][CH:15]([CH2:14][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:16]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18332937HCID 18332937, compound

Product 1

HCID 18333003HCID 18333003, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonyl chloride (0.65 ml) was added dropwise to an acetonitrile (20 ml) solution of 3-(pyrrolidin-1-yl)methyl-1, 2,3, 4-tetrahydroquinoline (Reference Example 47; 1.5 g) and triethylamine (2.9 ml) under ice-cooling. The reaction mixture was stirred at the same temperature for one hour, to which was added water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: hexane to hexane/ethylacetate=7/1). The crystals were washed with IPE to obtain the entitled compound (1.20 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by alumina column chromatography (eluent: hexane to hexane/ethylacetate=7/1)
  7. washThe crystals were washed with IPE

Sources & evidence

ORD record
ord-b6d2efac4c23412e90b89549ce1ae161
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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