Sodium Hydroxide → 3,5-Dichlorobenzyl 4-(2-((tert-butoxycarbonyl)amino)ethyl)piperidine-1-carboxylate

HRID 1480362Notes

Reaction equation

HRID 1480362 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[C:22](Cl)(=[O:33])[O:23][CH2:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=1.[OH-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:22]([O:23][CH2:24][C:25]2[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=2)=[O:33])[CH2:14][CH2:15]1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 15018494-(2-Aminoethyl)piperidine, 4-BOC protectedHCID 133055323,5-Dichlorobenzyl Chloroformate2×

Product 1

HCID 867226233,5-Dichlorobenzyl 4-(2-((tert-butoxycarbonyl)amino)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising of tert-butyl(2-(piperidin-4-yl)ethyl)carbamate (1.85 g, 8.10 mmol) in DCM (80 ml), sat. aqueous sodium bicarbonate solution (20 ml, 8.10 mmol) and 3,5-dichlorobenzyl carbonochloridate (prepared according to Bioorganic & Medicinal Chemistry Letters, 21(21), 6608-6612; 2011, Intermediate 33) (1.940 g, 8.10 mmol) was stirred at room temperature for 3 hours. The resulting mixture was treated with 2M NaOH soln. (50 ml). The organics were separated, dried (MgSO4) and concentrated under reduced pressure to afford the title compound;

Workup

  1. customThe organics were separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe9bbd015ea34ddfb41b931d1866019b
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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