4-Chlorobenzoyl chloride → HCID 15293229, compound

HRID 742583Notes

Reaction equation

HRID 742583 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-8f753ac0f3024198990f73d7867ec8c4
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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