Sodium Cyanide → HCID 86692812, compound

HRID 518638Notes

Reaction equation

HRID 518638 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:16]#[N:17].[Na+].C([O-])(O)=O.[Na+]>CCOCC.O>[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][C:12]([OH:15])([C:16]#[N:17])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 159326254-(Benzylamino)cyclohexan-1-one

Product 1

HCID 86692812HCID 86692812, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 4-(benzylamino)cyclohexanone (5.8 g, 28.5 mmol) in ether (112 mL) was cooled to 0° C. To this mixture was added NaCN (1.538 g, 31.4 mmol) as a solution in NaHCO3 (4.79 g, 57.1 mmol) and water (71.4 mL, 3966 mmol). The reaction mixture was stirred at RT for 16 hours. The resulting mixture was diluted with ether (110 mL) and water (50 mL). The layers were separated, and the organic portion was dried over sodium sulfate and concentrated under reduced pressure to afford 4-(benzylamino)-1-hydroxycyclohexanecarbonitrile as a light yellow solid (5.6 g, 85% yield). MS m/z=231.2 [M+H]. Calc'd for C14H18N2O: 230.1.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic portion was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e7afe71db394ee4980ac0773d32ba39
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…