Sodium Bicarbonate → 3,5-Dichlorobenzyl 4-(tert-butoxycarbonylamino)piperidine-1-carboxylate

HRID 1480391Notes

Reaction equation

HRID 1480391 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[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>C(Cl)Cl>[C:10]([O:9][C:8]([NH:7][CH:4]1[CH2:3][CH2:2][N:1]([C:20]([O:21][CH2:22][C:23]2[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=2)=[O:31])[CH2:6][CH2:5]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 133055323,5-Dichlorobenzyl Chloroformate

Product 1

HCID 680374753,5-Dichlorobenzyl 4-(tert-butoxycarbonylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl piperidin-4-ylcarbamate (2.0 g, 9.99 mmol) in DCM (40 ml) was treated with sodium bicarbonate solution (50 ml, 9.99 mmol) followed by a solution of 3,5-dichlorobenzyl carbonochloridate (2.392 g, 9.99 mmol) in DCM (10 ml). The reaction mixture was stirred vigorously at RT until gas evolution ceased. The organic layer was separated, dried over MgSO4 (anh), filtered and evaporated under reduced pressure, yielding the title compound as colourless oil that solidified on standing;

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4 (anh)
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6b41c62ec28f468cacabf036362c66d6
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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