Hydrochloric Acid → 5-Dimethylaminomethyl-spiro[2.5]octan-6-one

HRID 2404607Notes

Reaction equation

HRID 2404607 reaction equation
[CH2:1]1[C:3]2([CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)[CH2:2]1.Cl.[CH3:11][NH:12][CH3:13].Cl.[C:15]([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:11][N:12]([CH2:15][CH:7]1[C:6](=[O:9])[CH2:5][CH2:4][C:3]2([CH2:2][CH2:1]2)[CH2:8]1)[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 19371017Spiro[2.5]octan-6-one

Product 1

HCID 682910585-Dimethylaminomethyl-spiro[2.5]octan-6-oneYield 38.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Stir a mixture of spiro[2.5]octan-6-one (252 mg, 2.03 mmol), (HCHO)n (61 mg, 2.03 mmol), dimethylamine hydrochloride (166 mg, 2.03 mmol) and 0.3 mL of conc. HCl in MeCN (30 mL) at 60° C. for 6 hours. Quench the reaction with saturated aqueous NH4Cl solution (15 mL). Basify the aqueous solution with K2CO3 to pH=9. Extract the aqueous mixture with EtOAc (30 mL×2). The combined organic layers are washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated under vacuum. Purify the residue by silica gel chromatography (CH2Cl2:MeOH=30:1) to afford 5-Dimethylaminomethyl-spiro[2.5]octan-6-one as brown oil (142 mg, yield: 38.4%). MS (m/z): 182 (M+1).

Workup

  1. customQuench
  2. customthe reaction with saturated aqueous NH4Cl solution (15 mL)
  3. extractionExtract the aqueous mixture with EtOAc (30 mL×2)
  4. washThe combined organic layers are washed with brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customPurify the residue by silica gel chromatography (CH2Cl2:MeOH=30:1)

Sources & evidence

ORD record
ord-160760981cea4df69e69b837e687cdbb
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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