Sodium hydride → HCID 2724672, compound

HRID 2165113Notes

Reaction equation

HRID 2165113 reaction equation
CO[C:3]([CH:5]([CH3:22])[CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][CH2:9][C:10]([O:12][CH2:13]C)=[O:11])=[O:4].[H-].[Na+]>C1(C)C=CC=CC=1>[C:16]1([CH2:15][N:7]2[CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[C:3](=[O:4])[CH:5]([CH3:22])[CH2:6]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 98098N-(3-Methoxy-2-methyl-3-oxopropyl)-N-(phenylmethyl)-beta-alanine ethyl ester

Product 1

HCID 2724672HCID 2724672, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

N-[2-(Methoxycarbonyl)propyl]-N-[2-(ethoxycarbonyl)ethyl]phenylmethylamine (120.36g, 0.4 mole) from Example 2 in toluene (50 ml) was added slowly to a solution of 12 g (0.4 mole, 80% oil suspension) of sodium hydride in 300 ml of toluene. After the addition was complete, the temperature of the reaction solution was raised to 90° C. and maintained at this temperature overnight. After being cooled, the reaction solution was quenched with 200 ml of water, then extracted with ether to yield 98.54 g (70%) of the crude 1-phenylmethyl-3-methyl-5-methoxycarbonyl-4-piperidone.

Workup

  1. additionAfter the addition
  2. temperaturemaintained at this temperature overnight
  3. temperatureAfter being cooled
  4. customthe reaction solution was quenched with 200 ml of water
  5. extractionextracted with ether

Sources & evidence

ORD record
ord-8c8cda5fc1c642cb83ae17a0a744742d
Source dataset
uspto-grants-1990_07
Patent number
US04939161

Reaction notes

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