Phosgene → HCID 15700340, compound

HRID 2102719Notes

Reaction equation

HRID 2102719 reaction equation
[N:1]1([C:7](=[O:15])[CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:21](Cl)([Cl:23])=[O:22]>ClCCl>[N:1]1([C:7](=[O:15])[CH2:8][N:9]2[CH2:10][CH2:11][N:12]([C:21]([Cl:23])=[O:22])[CH2:13][CH2:14]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 1006221-(Morpholinocarbonylmethyl)piperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 15700340HCID 15700340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (0.5 g, 2.34 mmol) (Oakwood) in dichloromethane (15 mL) was added saturated sodium bicarbonate solution (15 mL). The reaction mixture was cooled to 0° C. and then followed by the dropwise addition of phosgene (20% in toluene, 2.22 mL, 4.21 mmol). The reaction mixture was allowed to warm up to room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was extracted with dichloromethane three times. The combined organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated to give crude 4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl chloride as yellow oil and used for the next step without further purification.

Workup

  1. temperatureto warm up to room temperature
  2. extractionthe reaction mixture was extracted with dichloromethane three times
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-84e9ae31a16544ea85731efe5b8e38a2
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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