Isopropyl chloroformate → HCID 11303575, compound

HRID 1860446Notes

Reaction equation

HRID 1860446 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][NH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32]>C1(C)C=CC=CC=1.CCOCC>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][NH:22][C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 10085886HCID 10085886, compound

Product 1

HCID 11303575HCID 11303575, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

22 g (75 mmol) of 1,4-dibenzyl-2-aminomethylpiperazine dissolved in 300 ml of toluene are mixed with 100 ml of triethylamine in a ground-necked conical flask. 97 ml (0.1 mol) of isopropyl chloroformate, taken up by syringe, are dissolved in 50 ml of toluene, and are then added dropwise to the above solution. At the end of the addition, the mixture is stirred for 2 hours at room temperature. The solution is diluted with ether, washed with saturated NaHCO3 solution and then with water to obtain a neutral pH. The organic phase is dried (MgSO4), filtered and evaporated to give 28.3 g of 1,4-dibenzyl-2-isopropyloxycarbonylaminomethylpiperazine in the form of a viscous compound. Yield: 99.6%. Rf=0.4 (95/5 v/v CH2Cl2/MeOH).

Workup

  1. additionare then added dropwise to the above solution
  2. additionAt the end of the addition
  3. washwashed with saturated NaHCO3 solution
  4. customwith water to obtain a neutral pH
  5. dry with materialThe organic phase is dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-761d2c98c19045a9b5335d31b351ff3f
Source dataset
uspto-grants-2003_03
Patent number
US06531476B1

Reaction notes

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