1-Chloroethyl chloroformate → HCID 69819501, compound

HRID 1006344Notes

Reaction equation

HRID 1006344 reaction equation
[C:1]([N:4]1[CH2:35][CH2:34][N:7]2[C@H:8]([CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9][N:10](CC3C=CC=CC=3OC)[CH2:11][C@@H:6]2[CH2:5]1)(=[O:3])[CH3:2].[Cl:36]C(OC(Cl)C)=O>ClC(Cl)C>[ClH:36].[ClH:36].[C:1]([N:4]1[CH2:35][CH2:34][N:7]2[C@H:8]([CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:9][NH:10][CH2:11][C@@H:6]2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 69819448HCID 69819448, compound

Product 1

HCID 69819501HCID 69819501, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (4R,9aR)-8-acetyl-4-benzhydryl-2-(2-methoxybenzyl)octahydro-2H-pyrazino[1,2-a]pyrazine (5.9 g) in dichloroethane (60 ml) was added 1-chloroethyl chloroformate (2.3 ml) at room temperature, and the reaction mixture was heated at 70° C. for 30 minutes with stirring. After removal of solvent by evaporation, to the resulting residue was added methanol (45 ml), and the solution was refluxed for 40 minutes. After being concentrated, the residue was triturated with diisopropyl ether. The resulting precipitate was collected by filtration and dried under, reduced pressure for 5 hours at 40° C. to give (4R,9aR)-8-acetyl-4-benzhydryloctahydro-2H-pyrazino[1,2-a]pyrazine dihydrochloride (3.1 g) as colorless foam.

Workup

  1. customAfter removal of solvent
  2. customby evaporation
  3. additionto the resulting residue was added methanol (45 ml)
  4. temperaturethe solution was refluxed for 40 minutes
  5. concentrationAfter being concentrated
  6. customthe residue was triturated with diisopropyl ether
  7. filtrationThe resulting precipitate was collected by filtration
  8. customdried under, reduced pressure for 5 hours at 40° C.

Sources & evidence

ORD record
ord-c25d63abeaac4d0cab8a9708aef2e573
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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