Sodium Bicarbonate → HCID 131733296, compound

HRID 515328Notes

Reaction equation

HRID 515328 reaction equation
C([N:3]([CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:4](=[O:10])[O:5][C:6]([CH3:9])(C)C)C.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:6]([O:5][C:4](=[O:10])[NH:3][CH:11]1[CH2:12][CH2:13][N:14]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([OH:34])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])=[CH:23][CH:24]=2)[CH2:15][CH2:16]1)[CH3:9]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18677728tert-Butyl ethyl(piperidin-4-yl)carbamateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 131733296HCID 131733296, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl ethyl(piperidin-4-yl)carbamate (10.95 mmol, 2.5 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (10.95 mmol, 3.69 g) and sodium hydrogencarbonate (16.42 mmol, 1.380 g) in acetonitrile (40 ml) was refluxed for 2 hours. The reaction was concentrated under reduced pressure and dichloromethane was added. The suspension was filtered and the filtrate was chromatographed on silica (eluting with a gradient of dichloromethane to ethyl acetate) to give the title compound (3.3 g). MS (ESI) m/z 485.1 [M+H]+

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction was concentrated under reduced pressure and dichloromethane
  3. additionwas added
  4. filtrationThe suspension was filtered
  5. customthe filtrate was chromatographed on silica (
  6. washeluting with a gradient of dichloromethane to ethyl acetate)

Sources & evidence

ORD record
ord-53140f3c5f664b4586f975dee8da09ca
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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