1,2-Diaminocyclohexane, trans- → HCID 15965747, compound

HRID 1883308Notes

Reaction equation

HRID 1883308 reaction equation
[C:1]1([P:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C@@H:22]1([NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]1[NH2:28]>C(O)C>[C:1]1([P:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH2:10][NH:28][C@@H:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C@H:22]2[NH2:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 438061,2-Diaminocyclohexane, trans-HCID 27543162-Diphenylphosphinobenzaldehyde

Product 1

HCID 15965747HCID 15965747, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution, heated to 45° C., of 2.5 g of 2-diphenylphosphanylbenzaldehyde (8.6 mmol) in 250 ml of absolute ethanol is added dropwise over a period of 16 hours to a solution of 3.3 g of (1R,2R)-cyclohexane-1,2-diamine (28 mmol) in 500 ml of absolute ethanol at 0° C. under a protective gas atmosphere. The reaction solution is stirred for one hour at 0° C. and 1.37 g of sodium hydridoborate (36 mmol) are then added. The reaction mixture is slowly allowed to rise to room temperature and stirred for a further 12 hours. The reaction is then quenched by adding 100 ml of acetone and the solvent is completely removed in a rotary evaporator. The resultant residue is completely dissolved by adding 100 ml of saturated ammonium hydrochloride solution and 100 ml of methylene chloride. The organic phase is then separated and washed three times with water. 100 ml of 10% hydrochloric acid are then poured on and the mixture shaken. After a short time in the refrigerator, the product crystallises out as a white mass (hydrochloride). After drying under a high vacuum, a yield of 2.54 g (70% of theoretical) is obtained.

Workup

  1. customto rise to room temperature
  2. stirringstirred for a further 12 hours
  3. customThe reaction is then quenched
  4. additionby adding 100 ml of acetone
  5. customthe solvent is completely removed in a rotary evaporator
  6. dissolutionThe resultant residue is completely dissolved
  7. additionby adding 100 ml of saturated ammonium hydrochloride solution and 100 ml of methylene chloride
  8. customThe organic phase is then separated
  9. washwashed three times with water
  10. addition100 ml of 10% hydrochloric acid are then poured on and the mixture
  11. stirringshaken
  12. customAfter a short time in the refrigerator, the product crystallises out as a white mass (hydrochloride)
  13. customAfter drying under a high vacuum
  14. customa yield of 2.54 g (70% of theoretical) is obtained

Sources & evidence

ORD record
ord-e552a5b6c1084a38b426b57be3f01bf3
Source dataset
uspto-grants-2004_07
Patent number
US06759559B2

Reaction notes

Loading…