1H-Indole-3-carbonyl chloride → N-((quinuclidin-4-yl)methyl)-1H-indole-3-carboxamide

HRID 1641013Notes

Reaction equation

HRID 1641013 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](Cl)=[O:11])=[CH:2]1.[N:13]12[CH2:20][CH2:19][C:16]([CH2:21][NH2:22])([CH2:17][CH2:18]1)[CH2:15][CH2:14]2>C(Cl)Cl>[N:13]12[CH2:20][CH2:19][C:16]([CH2:21][NH:22][C:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)=[O:11])([CH2:17][CH2:18]1)[CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 123802781H-Indole-3-carbonyl chlorideHCID 22056669Quinuclidin-4-ylmethanamine

Product 1

HCID 25210594N-((quinuclidin-4-yl)methyl)-1H-indole-3-carboxamideYield 14.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1H-indole-3-carbonyl chloride (112 mg, 0.625 mmol) in 3 mL of methylene chloride at 0° C. was added (quinuclidin-4-yl)methanamine (86 mg, 0.614 mmol) in 2 mL of methylene chloride. The mixture was stirred at room temperature overnight. The solvent was evaporated and water (20 mL) was added. The water layer was basified to pH 12 with 10% aqueous potassium hydroxide and extracted three times with 25 mL each of ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to yield 26 mg of the desired product. 1HNMR: 11.6 (bs, 1H); 8.15 (m, 1H); 8.13 (bs, 1H); 7.65 (bs, 1H); 7.42 (d, 1H); 7.15 (m, 2H); 3.1 (m, 2H); 2.65 (m, 6H); 1.40 (m, 6H). MS (m/e): 284.

Workup

  1. customThe solvent was evaporated
  2. additionwater (20 mL) was added
  3. extractionextracted three times with 25 mL each of ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-935233ec3bdd4a80b5731ff414d3c5a7
Source dataset
uspto-grants-2012_02
Patent number
US08114891B2

Reaction notes

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