Cyanogen Bromide → 4-Hydroxypiperidine-1-carbonitrile

HRID 532479Notes

Reaction equation

HRID 532479 reaction equation
C(=O)(O)[O-].[Na+].[OH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Br[C:14]#[N:15]>O.ClCCl>[OH:6][CH:7]1[CH2:12][CH2:11][N:10]([C:14]#[N:15])[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 79341Piperidin-4-olHCID 516892Sodium Bicarbonate

Product 1

HCID 218978254-Hydroxypiperidine-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Sodium bicarbonate was dissolved in water, and a solution of 4-hydroxypiperidine in dichloromethane and BrCN were added thereto at 0° C. The reaction mixture was stirred at 0° C. for 30 min and further stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was extracted twice with dichloromethane. The organic layer thus obtained was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound.

Workup

  1. customat 0° C
  2. stirringfurther stirred at room temperature for 2 hours
  3. customAfter completion of the reaction
  4. extractionthe reaction mixture was extracted twice with dichloromethane
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3fcc2a87400417280fa42596d3f0cbf
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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