Water → 1-Azabicyclo[4.3.1]decane-8-carbonitrile

HRID 65026Notes

Reaction equation

HRID 65026 reaction equation
[H-].[Na+].CC(C)([O-])C.[K+].Cl[CH2:10][CH:11]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]([CH2:18][CH2:19][C:20]#[N:21])[CH2:12]1.O>CN(C=O)C>[C:20]([CH:19]1[CH2:18][N:13]2[CH2:12][CH:11]([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:10]1)#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 20027694(+/-) 3-Chloromethyl-1-(2'-cyanoethyl)homopiperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 198486851-Azabicyclo[4.3.1]decane-8-carbonitrileYield 97.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred suspension of sodium hydride (1.5 g, 80%) and potassium t-butoxide (0.5 g) in DMF (100 ml) was added 3-chloromethyl-1-(2'-cyanoethyl)homopiperidine (D6) (5 g) and the reaction mixture was carefully warmed to 70° C. for 1 hour. On cooling, water (5 ml) was carefully added and the DMF was removed by rotary evaporation. Extraction of the residue with ethyl acetate, concentration and distillation afforded the (±) 8-cyano-1-azabicyclo-[4,3,1]-decane (D7) (4.0 g, 90%) bp 68°-73°/0.1 mm.

Workup

  1. temperatureOn cooling
  2. customthe DMF was removed by rotary evaporation
  3. extractionExtraction of the residue
  4. concentrationwith ethyl acetate, concentration and distillation

Sources & evidence

ORD record
ord-788fe01cb14042ddb0f096c255bd246f
Source dataset
uspto-grants-1986_09
Patent number
US04612319

Reaction notes

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