Triethylamine → HCID 57959915, compound

HRID 1698506Notes

Reaction equation

HRID 1698506 reaction equation
[CH2:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([NH2:20])[CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH2:2][CH3:3].C(N(CC)CC)C.[Cl:28][C:29]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>ClCCl.O>[Cl:28][C:29]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:30]=1[C:31]([NH:20][CH:13]([C:10]1[CH:11]=[CH:12][C:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[CH:8][CH:9]=1)[CH2:14][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 67275938HCID 67275938, compound

Product 1

HCID 57959915HCID 57959915, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {1-[4-(propylsulphonyl)phenyl]-2-pyrrolidin-1-ylethyl}amine (100 mg, 0.337 mmol) in dichloromethane (5 mL) under nitrogen was added triethylamine (47 □L, 0.337 mmol) followed by 2,4-dichlorobenzoyl chloride (47 □L, 0.336 mmol). The mixture was stirred at ambient temperature for 2 h, then diluted with water and extracted with ethyl acetate (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated. The product was purified by chromatography on silica eluting with 3% MeOH in dichloromethane to give the product as an off-white solid (123 mg, 78%). 1H NMR δ (400 MHz, CDCl3) δ 1.00 (3H, t, J=7.4 Hz), 1.69-1.81 (6H, m), 2.46-2.49 (2H, m), 2.58-2.62 (2H, m), 2.73 (1H, dd, J=12.5, 5.1 Hz), 2.91 (1H, dd, J=12.52, 9.5 Hz), 3.03-3.07 (2H, m), 5.01-5.09 (1H, m), 7.33 (1H, dd, J=8.3, 1.9 Hz), 7.46 (1H, d, J=1.9 Hz), 7.56 (2H, d, J=8.3 Hz), 7.64 (1H, d, J=8.3 Hz), 7.72 (1H, br d, J=3.9 Hz), 7.87 (2H, d, J=8.32 Hz); m/z (ES+) 471 (M+H), 469 (M+H), 400 (M-pyrrolidine), 398 (M-pyrrolidine).

Workup

  1. extractionextracted with ethyl acetate (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe product was purified by chromatography on silica eluting with 3% MeOH in dichloromethane

Sources & evidence

ORD record
ord-311c7f69648b445eaeb00e851a1b355e
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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