Dichloromethane → HCID 58911525, compound

HRID 1296302Notes

Reaction equation

HRID 1296302 reaction equation
ClC(OC(Cl)=O)C.COC1C=C(OC)C=CC=1C[N:13]1[CH2:26][CH:25]([CH3:27])[N:16]2[CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[CH2:24][C@@H:15]2[CH2:14]1.C(Cl)Cl.C([O-])(O)=O.[Na+]>ClCCCl>[CH3:27][CH:25]1[N:16]2[CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[CH2:24][C@@H:15]2[CH2:14][NH:13][CH2:26]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5213051-Chloroethyl chloroformateHCID 68691037HCID 68691037, compound

Product 1

HCID 58911525HCID 58911525, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Chloroethylchloroformate (0.050 ml, 0.47 mmol) was added to a solution of (11aR)-2,3,4,6, 11,11a-hexahydro-2-(2,4-dimethoxybenzyl)-4-methyl-1H-pyrazino[1,2-b]isoquinoline (53 mg, 0.15 mmol) in 1,2-dichloroethane (1 ml) stirring at 0° C. The ice bath was removed and the reaction stirred at ambient temperature for 30 min. After refluxing an additional 2 h, the reaction was evaporated in vacuo. Methanol (1.0 ml) was added to the residue and the reaction refluxed under nitrogen for 1 h. Evaporation in vacuo afforded 75 mg of crude product. This crude product was transferred to a separatory funnel with CH2Cl2 and saturated NaHCO3. Extraction with CH2Cl2 (2×) and drying of the combined organic layers over MgSO4 afforded 42 mg which was further purified by flash chromatography (SiO2, 0.2 to 10% 2N NH3 in MeOH/CH2Cl2) to give pure product (17 mg, 55%). MS (ESI) 203 (M+H).

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction stirred at ambient temperature for 30 min
  3. temperatureAfter refluxing an additional 2 h
  4. customthe reaction was evaporated in vacuo
  5. additionMethanol (1.0 ml) was added to the residue
  6. temperaturethe reaction refluxed under nitrogen for 1 h
  7. customEvaporation in vacuo
  8. customafforded 75 mg of crude product
  9. extractionExtraction with CH2Cl2 (2×)
  10. dry with materialdrying of the combined organic layers over MgSO4
  11. customafforded 42 mg which
  12. customwas further purified by flash chromatography (SiO2, 0.2 to 10% 2N NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6c76895d1dda4612b6ad62531ca19388
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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