Benzoyl chloride → HCID 18669060, compound

HRID 1058969Notes

Reaction equation

HRID 1058969 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[C:14]2[CH2:27][CH2:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30]>N1C=CC=CC=1>[C:1]([N:34]1[CH2:35][CH2:36][N:31]([C:29](=[O:30])[CH2:28][CH2:27][C:14]2[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([Cl:10])[CH:12]=3)[NH:16][C:15]=2[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:32][CH2:33]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 18669068HCID 18669068, compound

Product 1

HCID 18669060HCID 18669060, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (0.011 mL) was added to a stirred solution of 1-{3-[5-chloro-2-(4-chlorophenyl)-1H -indol-3-yl]-1-oxopropyl}piperazine (Description 30, 35 mg) in pyridine (0.5 mL) and the mixture was stirred at room temperature for 3 h. The solvent was evaporated under reduced pressure, hydrochloric acid (2M, 5 mL) and ethyl acetate (5 mL) were added and the layers were separated. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was crystallized from dichloromethane/ethyl acetate (4:1) to give the title compound as a colorless solid (25 mg, 58%). 1H NMR (360 MHz, CDCl3) δ2.56-2.68 (2H, m), 3.02-3.67 (10H, m), 7.17 (1H, dd, J 8.6, 1.8 Hz), 7.28 (1H, d, J 8.6 Hz), 7.33-7.50 (9H, m), 7.56 (1H, s), and 8.13 (1H, s). m/z (ES+) 506, 508 (M+1).

Workup

  1. customThe solvent was evaporated under reduced pressure, hydrochloric acid (2M, 5 mL) and ethyl acetate (5 mL)
  2. additionwere added
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was crystallized from dichloromethane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-fdf7d35f2711443e8471bd70c4569168
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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