HCID 21922995, compound → HCID 178492269, compound

HRID 1272628Notes

Reaction equation

HRID 1272628 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]2[CH:29]=[C:28]([O:30][CH3:31])[C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=2)[N:3]=1.[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([NH2:39])[CH2:35][CH2:34]1>O>[ClH:1].[ClH:1].[ClH:1].[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([NH:39][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]3[CH:29]=[C:28]([O:30][CH3:31])[C:24]4[O:25][CH2:26][O:27][C:23]=4[CH:22]=3)[N:3]=2)[CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 21922995HCID 21922995, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178492269HCID 178492269, compoundYield 523.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

The operation is carried out as in Stage 3 of Example 7 starting from 65 mg of the product obtained in Stage 1 above, 743 mg of trans-1,4-diaminocyclohexane, the reaction medium is heated to approximately 140° C. for 3 hours, followed by treating with 10 ml of water, extracting with 2×10 ml of ethyl acetate, washing with 10 ml of NaCl (saturated aqueous solution) and drying over MgSO4. Salification is carried out with 1.4N HCL/EtOH, followed by filtering, washing with 5 ml EtOH then drying at ˜50° C. In this way 161 mg of expected product is obtained.

Workup

  1. extractionextracting with 2×10 ml of ethyl acetate
  2. washwashing with 10 ml of NaCl (saturated aqueous solution)
  3. dry with materialdrying over MgSO4
  4. filtrationby filtering
  5. washwashing with 5 ml EtOH
  6. customthen drying at ˜50° C

Sources & evidence

ORD record
ord-b1acda5ccba24039a9c6238961b8a0d1
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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