Thionyl Chloride → HCID 66701167, compound

HRID 1253731Notes

Reaction equation

HRID 1253731 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)(O)[CH2:14][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[CH:14][CH2:13]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 59505451HCID 59505451, compound

Product 1

HCID 66701167HCID 66701167, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-benzyl-8-(pyridin-4-yl)-2-azaspiro[4.5]decan-8-ol (500 mg, 1.55 mmol, 1.0 eq.) (see step-7 product AMN-39) in pyridine (5 ml) was added dropwise SOCl2 (1 ml) at −10° C. and the reaction mixture was stirred at the same temperature for 10 min. After completion of the reaction (monitored by TLC), the reaction mixture was poured onto (50 g) and sat. NaHCO3 solution (10 ml) was added. The mixture was extracted with methylene chloride (50 ml). The organic layer was washed with brine (30 ml) and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product which was purified by column chromatography (silica gel; 2% MeOH/DCM) to yield the desired compound as a yellow semisold. Yield: 63% (300 mg, 0.987 mmol).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. additionwas added
  3. extractionThe mixture was extracted with methylene chloride (50 ml)
  4. washThe organic layer was washed with brine (30 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give the crude product which
  8. customwas purified by column chromatography (silica gel; 2% MeOH/DCM)

Sources & evidence

ORD record
ord-300c5027accf4cb78ad97e2942578a4f
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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