Hydrochloric Acid → 5-Nitro-2-piperidin-1-yl-benzoic acid

HRID 1833296Notes

Reaction equation

HRID 1833296 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 29424215-Nitro-2-piperidin-1-yl-benzoic acid

Procedure

30 Grams 2-chloro-5-nitrobenzoic acid was added in portions to 150 ml piperidine. The temperature of the reaction was allowed to rise during the addition. After the addition was complete, the reaction was heated at reflux temperature for two hours. The hot reaction mixture was poured into ice water, made acid by the addition of concentrated HCl until precipitation of the product was complete and filtered. The filter cake was recrystallized from ethanol to give 30.4 grams 5-nitro-2-piperidinobenzoic acid. m.p. = 201°-203° C. The nitro compound was reduced catalytically in ethanol with 5% palladium on carbon catalyst to give 5-amino-2-piperidinobenzoic acid. m.p. = 232°-235° C.

Workup

  1. additionto rise during the addition
  2. additionAfter the addition
  3. temperaturethe reaction was heated
  4. temperatureat reflux temperature for two hours
  5. customuntil precipitation of the product
  6. filtrationfiltered
  7. customThe filter cake was recrystallized from ethanol

Sources & evidence

ORD record
ord-a8d0302f8ef34e1185555e5e60ff99ce
Source dataset
uspto-grants-1978_01
Patent number
US04066457

Reaction notes

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