Hydrochloric Acid → HCID 46204980, compound

HRID 1643466Notes

Reaction equation

HRID 1643466 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][CH2:10][S:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH2:4]1.C(N(CC)CC)C.[CH3:34][O:35][C:36]1[CH:41]=[C:40]([CH3:42])[C:39]([S:43](Cl)(=[O:45])=[O:44])=[C:38]([CH3:47])[C:37]=1[CH3:48].C(=O)(O)[O-].[Na+].Cl.C[Si](C)(C)Cl>O1CCCC1.C(O)C>[CH3:34][O:35][C:36]1[CH:41]=[C:40]([CH3:42])[C:39]([S:43]([N:3]2[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][CH2:10][S:11]([N:14]3[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[CH2:18][CH2:19]3)(=[O:13])=[O:12])[CH2:4]2)(=[O:44])=[O:45])=[C:38]([CH3:47])[C:37]=1[CH3:48]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5627874-Methoxy-2,3,6-trimethylbenzenesulfonyl chlorideHCID 66754718HCID 66754718, compound

Product 1

HCID 46204980HCID 46204980, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-(Piperidin-3-yl)ethylsulfonyl)-4-(2-(pyrrolidin-1-yl)ethyl)piperidine dihydrochloride (0.15 g, 0.35 mmol) was dissolved in tetrahydrofuran (10 ml) under an inert gas, and triethylamine (0.15 ml, 1.05 mmol) and 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride (0.1 g, 0.42 mmol) were added. The mixture was refluxed for 2 h, saturated sodium bicarbonate solution (10 ml) was then added and the phases were separated. The aqueous phase was extracted with ethyl acetate (20 ml) and the combined organic phases were washed with saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25% aq) (300:100:1) and the hydrochloride was precipitated from an ethanol/ethereal solution with 1.2 eq of trimethylchlorosilane. Yield: 0.15 g (70%). MS, m/z=570.3 [MH]+

Workup

  1. additionwere added
  2. temperatureThe mixture was refluxed for 2 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  5. washthe combined organic phases were washed with saturated sodium chloride solution (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25% aq) (300:100:1)

Sources & evidence

ORD record
ord-d2e8198bf4bc44589e01f00443d681f1
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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