Benzoyl chloride → HCID 73009603, compound

HRID 1393004Notes

Reaction equation

HRID 1393004 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]3[C:13]4([CH2:14][CH2:15][C:4]=2[CH:3]=1)[CH:9]([CH2:10][N:11]([C:16](=[O:18])[CH3:17])[CH2:12]4)[CH2:8][CH2:7]3.C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:16]([N:11]1[CH2:12][C:13]23[CH:6]([CH2:7][CH2:8][CH:9]2[CH2:10]1)[C:5]1[CH:19]=[CH:20][C:2]([O:1][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:3][C:4]=1[CH2:15][CH2:14]3)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67422783HCID 67422783, compound

Product 1

HCID 73009603HCID 73009603, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Hydroxy-5,6,6a,7,10,11-hexahydro-4bH-benzo[4,5]indeno[1,7a-c]pyrrol-8-yl)-ethanone (Example 5B) (10.0 mg, 0.037 mmol) and triethylamine (15.4 μL, 0.11 mmol) were dissolved in CH2Cl2 (2 mL). Benzoyl chloride (5.1 μL, 0.044 mmol) was added dropwise. The mixture was stirred at rt for 12 hr, quenched with water (2 mL), and extracted with CH2Cl2 (5 mL×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane, providing 11.1 mg (80.4%) of the title compound.

Workup

  1. customquenched with water (2 mL)
  2. extractionextracted with CH2Cl2 (5 mL×3)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-6f60d2c930be4f06a85883671359903e
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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