1,2-Dichloroethane → HCID 68819908, compound

HRID 734316Notes

Reaction equation

HRID 734316 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O-:16])=O)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)C[Cl:19].C1C=NC2N(O)N=NC=2C=1.[CH:31]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)([CH3:33])[CH3:32]>CN(C=O)C.CCOC(C)=O>[ClH:19].[ClH:19].[CH:31]([N:34]1[CH2:39][CH2:38][N:37]([C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:16])[CH2:36][CH2:35]1)([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 780131-IsopropylpiperazineHCID 181649HOAtHCID 6921829HCID 6921829, compound

Product 1

HCID 68819908HCID 68819908, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-tert-Butoxycarbonyl-piperidine-4-carboxylate (5 g) in DMF (60 ml) was treated with EDC (5.5 g) followed by HOAT (0.1 g). After 5 min, N-isopropylpiperazine (2.8 g) in DMF (5 ml) was added and the reaction was left stirring for 18 h. The reaction was then diluted with EtOAc (150 ml) and washed with saturated brine/sodium hydrogen carbonate (1:1, 200 ml) followed by brine (3×200 ml). The EtOAc layer was evaporated to near dryness and the residue treated with TFA/water (40 ml, 95:5) for 5 h prior to evaporation and re-evaporation from toluene (3×60 ml). The residue was taken up into a minimum volume of EtOAc and treated with HCl (30 ml, 2N solution in diethyl ether) for 1 h. The resulting sub-titled compound was filtered off and washed with diethyl ether before drying under vacuum (4.8 g).

Workup

  1. waitthe reaction was left
  2. washwashed with saturated brine/sodium hydrogen carbonate (1:1, 200 ml)
  3. customThe EtOAc layer was evaporated
  4. additionthe residue treated with TFA/water (40 ml, 95:5) for 5 h
  5. customto evaporation and re-evaporation from toluene (3×60 ml)
  6. additiontreated with HCl (30 ml, 2N solution in diethyl ether) for 1 h
  7. filtrationThe resulting sub-titled compound was filtered off
  8. washwashed with diethyl ether
  9. custombefore drying under vacuum (4.8 g)

Sources & evidence

ORD record
ord-a4a6784999f64e1ab5fe76db8a036040
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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