Dimethylamine → N,N-Dimethyl-1,4-dioxaspiro[4.5]decan-8-amine

HRID 2395521Notes

Reaction equation

HRID 2395521 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[CH3:12][NH:13][CH3:14].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][CH:7]([N:13]([CH3:14])[CH3:12])[CH2:6][CH2:5]2)[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 361167N,N-Dimethyl-1,4-dioxaspiro[4.5]decan-8-amineYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5.0 gm (32 mMol) 1,4-cyclohexanedione mono-ethylene ketal and 10.80 gm (240 mMol) dimethylamine were added 2.0 mL acetic acid and the mixture was stirred at 0° C. for 1.5 hours. To this solution were then added 3.62 gm (58 mMol) sodium cyanoborohydride and the reaction stirred for an additional hour at ambient. The pH of the reaction mixture was adjusted to ~7 with 16 mL acetic acid and stirred 18 hours at ambient. The volatiles were removed under reduced pressure and the residue dissolved in cold 5% tartaric acid solution and then the aqueous phase was made basic with 5N sodium hydroxide. This aqueous phase was extracted well with dichloromethane. These organic extracts were combined and concentrated under reduced pressure to give 5.04 gm (85%) of the title compound as an oil.

Workup

  1. stirringthe reaction stirred for an additional hour at ambient
  2. stirringstirred 18 hours at ambient
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue dissolved in cold 5% tartaric acid solution
  5. extractionThis aqueous phase was extracted well with dichloromethane
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7f01af25c504fc1802c6acecb992a25
Source dataset
uspto-grants-1998_09
Patent number
US05814653

Reaction notes

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