4-Chlorobenzoyl chloride → HCID 15293229, compound

HRID 233036Notes

Reaction equation

HRID 233036 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(#N)C.ClCCl>[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:1][CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][CH2:6][CH:5]2[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[O:29])=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 23361315N-(2-aminoethyl)-2-(3-methoxyphenyl)pyrrolidine

Product 1

HCID 15293229HCID 15293229, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-aminoethyl)-2-(3-methoxyphenyl)pyrrolidine (0.58 g) in acetonitrile (15 ml) was added milled potassium carbonate (1.10 g) followed by 4-chlorobenzoyl chloride (0.33 ml) at ambient temperature, under nitrogen. The reaction mixture was stirred for 1.5 hrs, diluted with dichloromethane, and filtered. The filter cake was washed with dichloromethane, and the combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, 0-20% methanol/dichloromethane). The appropriate fractions were collected and concentrated to afford 0.80 g (85%) of product. Trituration with ether/petroleum ether gave the analytical sample, mp 96°-98° C.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with dichloromethane
  3. concentrationthe combined filtrates were concentrated
  4. customThe residue was purified by flash column chromatography (silica gel, 0-20% methanol/dichloromethane)
  5. customThe appropriate fractions were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7e91b21527c14cea9beb820c9d6229a9
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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