Benzaldehyde → HCID 11119970, compound

HRID 1011660Notes

Reaction equation

HRID 1011660 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@H:9]1([NH2:16])[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1N.[BH3-][C:18]#[N:19].[Na+]>CO>[CH2:1]([NH:16][C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]1[NH:19][CH2:18][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4793071,2-Diaminocyclohexane, (+)-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 11119970HCID 11119970, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzaldehyde (6.36 g, 60 mmol) was added dropwise over a period of 2 minutes to a solution of (S,S)-cyclohexane-1,2-diamine (3.42 g, 30 mmol) in 50 mL of anhydrous MeOH at refluxing temperature. After stirring for 30 min, the solution was allowed to cool to room temperature and NaBH3CN (2.4 g, 63 mmol) was added in portions. After the vigorous effervescence subsided down, the mixture was brought to refluxing and stirred for 20 min. The reaction was quenched by water and extracted with dichloromethane. The organic phase was dried and concentrated to give 8.5 g of crude product (yield 95%) which was used in the next step reaction without further purification.

Workup

  1. temperatureat refluxing temperature
  2. temperatureto refluxing
  3. stirringstirred for 20 min
  4. customThe reaction was quenched by water
  5. extractionextracted with dichloromethane
  6. customThe organic phase was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-83ff41484cc74244a8bd2b31f99f1473
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

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