Dichloromethane → HCID 19975171, compound

HRID 1975239Notes

Reaction equation

HRID 1975239 reaction equation
Cl[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]([CH2:21][CH3:22])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11](=[O:23])[NH:10][C:9]1=[O:24])=[O:3].[N:25]1([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(CC)CC)C.ClCCl>C(Cl)(Cl)Cl>[CH2:34]([O:33][C:31]([N:25]1[CH2:30][CH2:29][N:28]([C:2]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]2[C:13](=[O:14])[C:12]([CH2:21][CH3:22])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11](=[O:23])[NH:10][C:9]2=[O:24])=[O:3])[CH2:27][CH2:26]1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 643495Benzyl piperazine-1-carboxylateHCID 19975168HCID 19975168, compound

Product 1

HCID 19975171HCID 19975171, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The acid chloride of step 3 (0.2 mole) in chloroform (75 mL) was added dropwise over 15 minutes to a mixture of benzyl 1-piperazinecarboxylate (6.0 g, 0.030 mole) and triethylamine (4.0 g, 0.04 mole) in chloroform (100 mL). This mixture was stirred at room temperature for 20 hrs, and dichloromethane was then added (300 mL). The mixture was washed with 10% hydrochloric acid solution (3×100 mL), washed with saturated sodium chloride solution (100 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent removed. The residue was then chromatographed on SiO2 to give a solid.

Workup

  1. washThe mixture was washed with 10% hydrochloric acid solution (3×100 mL)
  2. washwashed with saturated sodium chloride solution (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed
  6. customThe residue was then chromatographed on SiO2
  7. customto give a solid

Sources & evidence

ORD record
ord-dfcab305246c401d94a2bcdadcc7bf25
Source dataset
uspto-grants-1994_02
Patent number
US05284948

Reaction notes

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