Hydrochloric Acid → 3-(aminomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

HRID 655912Notes

Reaction equation

HRID 655912 reaction equation
[N:1]([CH2:4][C:5]1[C:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([NH:17][C@H:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:19][CH3:20])=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+]=[N-].Cl>C(O)C.[Pd]>[NH2:1][CH2:4][C:5]1[C:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([NH:17][C@H:18]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:19][CH3:20])=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 578935703-(azidomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

Product 1

HCID 578935693-(aminomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamideYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(azidomethyl)-2-phenyl-N-[(1s)-1-phenylpropyl]quinoline-4-carboxamide (2d) (1000 mg, 2.37 mmol) in ethanol (200 mL) were added Pd/C (10%, 1190 mg) and HCl (2N, 2.5 mL) was added. The reaction mixture were hydrogenated under 50 psi H2 at RT for 1.5 h. The catalyst was removed by filtration through a thick layer of diatomaceous earth, the filter was washed with ethanol and the washes and the ethanol solvent was combined and concentrated in vacuo. Crystallization from dichloromethane and ether afforded the title compound (940 mg, 92%) as a hydrogen chloride salt. 1H NMR (300 MHz, CDCl3) δ 0.92 (t, 3H), 2.01 (m, 2H), 3.18 (b, 3H), 4.39 (t, 2H), 5.16 (q, 1H), 7.30 (d, 2H), 7.34 (d, 2H), 7.39 (m, 1H), 7.78 (m, 2H), 7.84 (m, 2H), 8.08 (m, 1H), 8.30 (m, 2H), 8.44 (m, 2H). MS APCI, m/z=396 (M+1). LCMS: 1.70 min.

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration through a thick layer of diatomaceous earth
  3. washthe filter was washed with ethanol
  4. concentrationconcentrated in vacuo
  5. customCrystallization from dichloromethane and ether

Sources & evidence

ORD record
ord-b8a6ed57d06f4d7d8d356ea92e884487
Source dataset
uspto-grants-2011_12
Patent number
US08071621B2

Reaction notes

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