Sodium Bicarbonate → 3,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)piperidine-1-carboxylate

HRID 1480447Notes

Reaction equation

HRID 1480447 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:16](Cl)(=[O:27])[O:17][CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:16]([O:17][CH2:18][C:19]2[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=2)=[O:27])[CH2:13][CH2:14]1)=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 133055323,5-Dichlorobenzyl Chloroformate

Product 1

HCID 867226733,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture comprising tert-butyl(piperidin-4-ylmethyl)carbamate (1 g, 4.67 mmol), 3,5-dichlorobenzyl carbonochloridate, (1.117 g, 4.67 mmol) and sodium bicarbonate (15 mL, 4.67 mmol) in DCM (15.55 mL) was stirred at room temperature for 18 hours. The reaction mixture was separated and the organic portion was dried over MgSO4, filtered and solvent concentrated under reduced pressure to give the title compound as a yellow oil;

Workup

  1. customThe reaction mixture was separated
  2. dry with materialthe organic portion was dried over MgSO4
  3. filtrationfiltered
  4. concentrationsolvent concentrated under reduced pressure

Sources & evidence

ORD record
ord-fecbfd67cca84c1982b42e36489e7067
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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