Dichloromethane → (R)-1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(1-phenylethyl)piperidine-4-carboxamide

HRID 83602Notes

Reaction equation

HRID 83602 reaction equation
F[C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:59]1([C@H:65]([NH2:67])[CH3:66])[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.C(Cl)[Cl:69]>O.C(OCC)(=O)C>[Cl:69][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:67][C@@H:65]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[CH3:66])=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:27][CH:28]=1

Participants

9

Reactant 6

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6431891-Phenethylamine, (+)-HCID 683797351-(1-(4-fluorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 56929805(R)-1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(1-phenylethyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-fluorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.263 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (76 mg, 0.394 mmol), and 1-Hydroxybenzotriazole (53 mg, 0.394 mmol) were dissolved in 3.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (68.9 μL, 0.504 mmol) and (R)-1-phenylethanamine (64 μL, 0.504 mmol) were added. The reaction was allowed to stir for 48 hours. The reaction was diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with another aliquot of water. The ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated in methanol, filtered and dried under vacuum to obtain pure product as a white solid. Yield: 32.9 mg (White solid)

Workup

  1. additionwere added
  2. customThe layers were separated
  3. washthe organic layer was washed with another aliquot of water
  4. washThe ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was triturated in methanol
  9. filtrationfiltered
  10. customdried under vacuum
  11. customto obtain pure product as a white solid

Sources & evidence

ORD record
ord-47c8b8809c0147579a94319072e99181
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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