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

HRID 1480396Notes

Reaction equation

HRID 1480396 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[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:5]([O:4][C:3]([N:2]([CH3:1])[CH:10]1[CH2:11][CH2:12][N:13]([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])[CH2:14][CH2:15]1)=[O:9])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 133055323,5-Dichlorobenzyl Chloroformate

Product 1

HCID 867226393,5-Dichlorobenzyl 4-((tert-butoxycarbonyl)(methyl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl methyl(piperidin-4-yl)carbamate (1.25 g, 5.83 mmol), 3,5-dichlorobenzyl carbonochloridate (1.537 g, 6.42 mmol) and sat. sodium bicarbonate (0.583 ml, 5.83 mmol) in DCM (15 ml) was stirred at RT for 72 hrs. The resulting mixture was extracted with DCM and the combined organic extracts were dried over MgSO4, filtered and concentrated under pressure to afford the title compound which was used without further purification.

Workup

  1. extractionThe resulting mixture was extracted with DCM
  2. dry with materialthe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under pressure

Sources & evidence

ORD record
ord-bb9d3f4cee5f4dfc880de00c71cbc831
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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