Methanesulfonyl chloride → HCID 15166857, compound

HRID 727799Notes

Reaction equation

HRID 727799 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][CH2:13][CH2:14]O)[CH:2]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[C:30]1([C:36]2[CH2:37][CH2:38][NH:39][CH2:40][CH:41]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1>[C:30]1([C:36]2[CH2:41][CH2:40][N:39]([CH2:14][CH2:13][CH2:12][CH2:11][C:3]3[CH:2]=[N:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:38][CH:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 516892Sodium BicarbonateHCID 15166840HCID 15166840, compound

Product 1

HCID 15166857HCID 15166857, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
0 °C

Procedure

A solution of 4-(3-quinolinyl)butan-1-ol (Example E) (2.0 g, 0.01 mol), N,N diisopropylethylamine (3.5 mL, 0.02 mol) and a catalytic amount of 4-dimethylaminopyridine is cooled to 0° C. and methanesulfonyl chloride (0.8 mL, 0.0105 mol) is added dropwise. The solution is stirred at 0° C. for 18 hours, and concentrated under reduced pressure. The residue is taken up in dimethylformamide (20 mL), and to this solution is added 4-phenyl-1,2,3,6-tetrahydropyridine (2.41 g, 0.015 mol) and sodium bicarbonate (3.4 g, 0.04 mol). The mixture is heated at 40° C. for 5 hours and the solvent removed under reduced pressure. The residue is partitioned between 50 mL of ethyl acetate and 50 mL of water. The aqueous layer is extracted with 50 mL of ethyl acetate and the organic extracts are dried (sodium sulfate) and the solvent removed in vacuo. The residue is chromatographed (silica gel, 2% methanol/98% dichloromethane) to give 2.15 g of the title compound; mp 92.8°-93.9° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperatureThe mixture is heated at 40° C. for 5 hours
  3. customthe solvent removed under reduced pressure
  4. customThe residue is partitioned between 50 mL of ethyl acetate and 50 mL of water
  5. extractionThe aqueous layer is extracted with 50 mL of ethyl acetate
  6. dry with materialthe organic extracts are dried (sodium sulfate)
  7. customthe solvent removed in vacuo
  8. customThe residue is chromatographed (silica gel, 2% methanol/98% dichloromethane)

Sources & evidence

ORD record
ord-7545263c0bcd4be29e7d1651f1af788f
Source dataset
uspto-grants-1991_09
Patent number
US05045550

Reaction notes

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