Benzaldehyde → HCID 21969251, compound

HRID 1422055Notes

Reaction equation

HRID 1422055 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:8].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+]>CO.ClCCl>[CH2:9]([NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 438061,2-Diaminocyclohexane, trans-HCID 4311764Sodium borohydride

Product 1

HCID 21969251HCID 21969251, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

60.0 g (525.4 mmol) of (±)-trans-1,2-diaminocyclohexane is dissolved in 750 ml of absolute methanol and cooled to 0° C. At this temperature, the drop-by-drop addition of 10.5 g (99 mmol) of benzaldehyde, dissolved in 100 ml of absolute methanol, is carried out. After a reaction time of 2 hours at 0° C., the addition in portions of a total of 3.74 g (99 mmol) of sodium borohydride is carried out. After 12 hours at 25° C., the reaction solution is suctioned off on diatomaceous earth, and the solvent is drawn off in a vacuum. The remaining oily residue is taken up in 500 ml of dichloromethane and washed three times with 100 ml of water each. After the organic phase is dried on sodium sulfate, the solvent is drawn off in a vacuum. The oily residue that is thus obtained is chromatographed on silica gel (eluant: methanol/aqueous ammonia solution 20:1).

Workup

  1. washwashed three times with 100 ml of water each
  2. customAfter the organic phase is dried on sodium sulfate
  3. customThe oily residue that is thus obtained
  4. customis chromatographed on silica gel (eluant: methanol/aqueous ammonia solution 20:1)

Sources & evidence

ORD record
ord-1072c065c13746778155b46e4271006c
Source dataset
uspto-grants-2000_06
Patent number
US06080785

Reaction notes

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