Triethylamine → HCID 90044660, compound

HRID 1050239Notes

Reaction equation

HRID 1050239 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl.CN(C1C=CN=CC=1)C.[NH4+].[Cl-].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 90044660HCID 90044660, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 57429219Ammonium chloride monohydrateSolvent

Procedure

4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine (645 mg, 3.33 mmol) was dissolved in DCM (20 ml) and then DMAP (40.7 mg, 0.333 mmol), triethylamine (1.858 ml, 13.33 mmol), and methane sulfonylchloride (0.286 ml, 3.67 mmol) were added. The reaction was stirred 1 h at rt, then diluted with DCM and saturated NH4Cl/water (1:1). The aqueous phase was extracted with DCM (×2) and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 10% to 100% EtOAc:Hexane to provide the desired product. LC-MS: calculated for C12H14ClNO2S 271.04 observed m/e: 271.91 (M+H)+ (Rt 1.15/2 min).

Workup

  1. extractionThe aqueous phase was extracted with DCM (×2)
  2. washthe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography on a Biotage™ 50 g column
  7. washby eluting with 10% to 100% EtOAc

Sources & evidence

ORD record
ord-b08da01a9a694a4698aea22b328ed3ce
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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