Benzaldehyde → 1R,2R-N,N'-bis(phenylMethyl)-1,2-CyclohexanediaMine

HRID 1011659Notes

Reaction equation

HRID 1011659 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 438061,2-Diaminocyclohexane, trans-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 111409571R,2R-N,N'-bis(phenylMethyl)-1,2-CyclohexanediaMineYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzaldehyde (12.72 g, 120 mmol) was added dropwise over a period of 2 minutes to a solution of (R,R)-cyclohexane-1,2-diamine (6.84 g, 60 mmol) in 100 mL of anhydrous MeOH at refluxing temperature. After stirring for 30 min, the solution was allowed to cool to room temperature and NaBH3CN (4.8 g, 126 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 16.95 g of crude product (yield 96%) 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-412e03eb004848a6b1f56f379598f93b
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

Loading…