Sodium hydride → HCID 58878508, compound

HRID 1441667Notes

Reaction equation

HRID 1441667 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Br:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Br:22])[CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-HCID 15442175HCID 15442175, compound

Product 1

HCID 58878508HCID 58878508, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-Bromo-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 2.60 mmol) was dissolved in dry N,N-dimethylformamide (10.0 mL). To the reaction mixture was then added at 0° C. sodium hydride (60% in mineral oil, 127.3 mg, 3.18 mmol) under nitrogen atmosphere and the reaction mixture was stirred at 0° C. for one hour. To the reaction mixture was then added at 0° C., bromomethyl-cyclohexane (0.55 g, 3.13 mmol). The reaction mixture was stirred at 0° C. for one hour, then at room temperature under nitrogen atmosphere for 18 hours. The reaction mixture was then added into an excess of water-ice and a solid precipitated. The solid was filtered by suction, washed with water and dried to yield a crude solid. The crude solid was purified via flash chromatography (25% ethyl acetate/hexanes) to yield the title compound as a solid.

Workup

  1. additionTo the reaction mixture was then added at 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for one hour
  3. waitat room temperature under nitrogen atmosphere for 18 hours
  4. customa solid precipitated
  5. filtrationThe solid was filtered by suction
  6. washwashed with water
  7. customdried
  8. customto yield a crude solid
  9. customThe crude solid was purified via flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6be3c894e20d40c88f9c8a225017aaa7
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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