p-Anisoyl chloride → HCID 10273336, compound

HRID 914768Notes

Reaction equation

HRID 914768 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH2:12][CH2:11]1)=[O:9])[CH:5]([CH3:7])[CH3:6].C(N(CC)CC)C.[C:30](Cl)(=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([C:30]([NH:3][C@@H:4]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]3[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]3)[CH2:12][CH2:11]2)=[O:9])[CH:5]([CH3:6])[CH3:7])=[O:39])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 69143472HCID 69143472, compound

Product 1

HCID 10273336HCID 10273336, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-D-Valinyl-4-(1-methylpiperidin-4-yl)piperidine dihydrochloride (15.6 g, 44.1 mmol) is slurried in anhydrous CH2Cl2 (400 mL); and to the slurry is added triethylamine (19.7 mL, 141.0 mmol), followed by p-anisoyl chloride (7.9 mL, 52.9 mmol). The reaction is allowed to stir for about 30 min and then quenched with the addition of saturated NaHCO3 (300 mL), followed by the separation of the phases. The organic layer is washed with saturated NaHCO3 (2×300 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified by chromatography over silica gel, eluting with 2.5% (2 M NH3 in MeOH)/CHCl3 to give 16.3 g (89%) of the title compound as a white foam.

Workup

  1. customquenched with the addition of saturated NaHCO3 (300 mL)
  2. customfollowed by the separation of the phases
  3. washThe organic layer is washed with saturated NaHCO3 (2×300 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by chromatography over silica gel
  8. washeluting with 2.5% (2 M NH3 in MeOH)/CHCl3

Sources & evidence

ORD record
ord-eb64c335ce7541b69acf4af0f9b4e7de
Source dataset
uspto-grants-2007_09
Patent number
US07265121B2

Reaction notes

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