Methyl chloroformate → HCID 15645978, compound

HRID 1196873Notes

Reaction equation

HRID 1196873 reaction equation
[CH3:1][O:2][C:3](Cl)=[O:4].Cl.Cl.[Cl:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH:20]2[CH2:25][N:26]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27]2)=[O:18])[CH:12]=[CH:13][C:14]=1[Cl:15].C(N(CC)CC)C>ClCCl>[NH3:19].[Cl:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:3]([O:2][CH3:1])=[O:4])[CH2:21][CH:20]2[CH2:25][N:26]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27]2)=[O:18])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 22707193HCID 22707193, compound

Product 2

HCID 222AmmoniaHCID 15645978HCID 15645978, compoundYield 165.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methylchloroformate (243 mg) in dry dichloromethane (3 ml) was added dropwise to a stirred solution of 1-[(3,4-dichlorophenyl)acetyl]-2-[(3-hydroxy-1-pyrrolidinyl)methyl]piperazine dihydrochloride (1.0 g) and triethylamine (495 mg) in dry dichloromethane (25 ml) at -25° under nitrogen. The resulting solution was stirred at -30°--25° for 30 min, quenched with aqueous 2N sodium carbonate solution (30 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried and evaporated to give a foam. The residue was purified by flash column chromatography eluting with dichloromethane:methanol:0.880 NH3 (150:8:1) to give the title compound as a foam (800 mg).

Workup

  1. customquenched with aqueous 2N sodium carbonate solution (30 ml)
  2. extractionextracted with dichloromethane (3×20 ml)
  3. customThe combined organic extracts were dried
  4. customevaporated
  5. customto give a foam
  6. customThe residue was purified by flash column chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-4b886852f2db42a794cadb5538217d03
Source dataset
uspto-grants-1992_05
Patent number
US05116842

Reaction notes

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