Sodium Hydroxide → HCID 178520583, compound

HRID 1480500Notes

Reaction equation

HRID 1480500 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:19])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[N:15]=[N:16][NH:17][CH:18]=2)[CH2:3][CH2:2]1.[C:20](Cl)(=[O:31])[O:21][CH2:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=1.[OH-].[Na+]>C(Cl)Cl>[NH:17]1[CH:18]=[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([NH:7][CH:4]2[CH2:3][CH2:2][N:1]([C:20]([O:21][CH2:22][C:23]3[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=3)=[O:31])[CH2:6][CH2:5]2)=[O:19])[N:15]=[N:16]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 178520582HCID 178520582, compound

Product 1

HCID 178520583HCID 178520583, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(Piperidin-4-yl)-6-(1H-1,2,3-triazol-4-yl)hexanamide (135 mg, 0.509 mmol) in DCM (50 ml) was treated with 3,5-dichlorobenzyl carbonochloridate (134 mg, 0.560 mmol) and 2M sodium hydroxide (25 ml, 50 mmol). The reaction mixture was stirred at room temperature for 5 hrs. The organics were removed, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by mass directed preparative LC to give the title compound, after concentration of the relevant fractions.

Workup

  1. customThe organics were removed
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by mass

Sources & evidence

ORD record
ord-7c5f9ae45829477bb5e60611da5e6ed2
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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