Acetone → HCID 20195513, compound

HRID 653100Notes

Reaction equation

HRID 653100 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[Br:12]C[C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([N+:22]([O-:24])=[O:23])=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:18]=2[CH:31]=1.CC(C)=O>C(OCC)C>[BrH:12].[N+:22]([C:20]1[O:21][C:17]2[CH:16]=[CH:15][C:14]([N:1]3[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]3)=[CH:31][C:18]=2[C:19]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 180AcetoneHCID 70770Ethyl 4-piperidinecarboxylateHCID 13531604HCID 13531604, compound

Product 1

HCID 20195513HCID 20195513, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.04 g. (0.0066 mole) of ethyl isonipecotate and 2 g. (0.006 mole) of 5-bromomethyl-2-nitro-3-phenylbenzofuran in 100 ml. of acetone is heated at reflux for 40 hours. The mixture is cooled and then evaporated to provide a residue which is diluted with diethyl ether. A yellow precipitate is separated by filtration to provide ethyl N-(2-nitro-3-phenylbenzofuran-5-yl)isonipecotate hydrobromide, m.p. 220°-221° C., having the structure

Workup

  1. additionA mixture of 1.04 g
  2. temperatureat reflux for 40 hours
  3. temperatureThe mixture is cooled
  4. customevaporated
  5. customto provide a residue which
  6. customA yellow precipitate is separated by filtration

Sources & evidence

ORD record
ord-355f479a7ba14f3ea5903ea9850443f0
Source dataset
uspto-grants-1987_06
Patent number
US04675320

Reaction notes

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