Thionyl Chloride → HCID 66700616, compound

HRID 1253734Notes

Reaction equation

HRID 1253734 reaction equation
O=S(Cl)Cl.[CH2:5]([N:12]1[CH2:16][CH2:15][C:14]2([CH2:21][CH2:20][C:19]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)(O)[CH2:18][CH2:17]2)[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH2:5]([N:12]1[CH2:16][CH2:15][C:14]2([CH2:21][CH2:20][C:19]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:18][CH2:17]2)[CH2:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66700982HCID 66700982, compound

Product 1

HCID 66700616HCID 66700616, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

SOCl2(1 ml) was added dropwise to a solution of 2-benzyl-8-(pyridin-3-yl)-2-azaspiro[4.5]decan-8-ol (450 mg, 1.39 mmol, 1.0 eq.) in pyridine (5 ml) at −10° C. and the reaction mixture was stirred at the same temperature for 15 min. After completion of the reaction (monitored by TLC), the reaction mixture was poured onto crushed ice and the mixture was then neutralized with sat. NaHCO3 solution (15 ml). It was extracted with methylene chloride (2×30 ml) and the combined organic layers were washed with water (20 ml) and brine (20 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; 10% MeOH/DCM) to yield the desired compound as a reddish sticky solid. Yield: 71% (300 mg, 0.99 mmol).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. additionthe reaction mixture was poured
  3. customonto crushed ice
  4. extractionIt was extracted with methylene chloride (2×30 ml)
  5. washthe combined organic layers were washed with water (20 ml) and brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customto give the crude product which
  9. customwas purified by column chromatography (silica gel; 10% MeOH/DCM)

Sources & evidence

ORD record
ord-8bc08d705ae24aa3b25c0eae28bfec27
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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