1,2-Diaminocyclohexane, (+)- → HCID 178478707, compound

HRID 1453581Notes

Reaction equation

HRID 1453581 reaction equation
[N:1]1([C:10]2[N:18]=[C:17]([Cl:19])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH2:20][C@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]1[NH2:27]>CS(C)=O>[ClH:19].[ClH:19].[N:1]1([C:10]2[N:18]=[C:17]([NH:20][C@@H:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]3[NH2:27])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4793071,2-Diaminocyclohexane, (+)-HCID 178478376HCID 178478376, compound

Product 1

HCID 178478707HCID 178478707, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

200 mg of product obtained in stage 1 above are mixed with 3 ml of DMSO and 420 mg (5 equivalents) of (1S,2S)-(−)-1,2-diaminocyclohexane, and the mixture is then heated at 120° C. for approximately 4 days. The mixture is allowed to return to ambient temperature. Purification is carried out by chromatography on silica with a CH2Cl2-MeOH—NH4OH: 95-5-0.33 mixture for eluent. 4 ml of ethanol and 4 ml of HCl-EtOH (hydrochloric acid-ethanol) are added. Evaporation to dryness is carried out and a paste is then formed in ethyl ether. Drying is carried out under vacuum. 116 mg of expected product are obtained.

Workup

  1. customto return to ambient temperature
  2. customPurification
  3. addition4 ml of ethanol and 4 ml of HCl-EtOH (hydrochloric acid-ethanol) are added
  4. customEvaporation to dryness
  5. customa paste is then formed in ethyl ether
  6. customDrying

Sources & evidence

ORD record
ord-4ead75426e3b491f838e88222ec25956
Source dataset
uspto-grants-2009_01
Patent number
US07476670B2

Reaction notes

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