HCID 21543532, compound → HCID 21442848, compound

HRID 1606513Notes

Reaction equation

HRID 1606513 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[C:6]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH2:13][CH2:12]1)=[O:7])([O-])=O>[Pd].CO>[C:6]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH2:13][CH2:12]1)(=[O:7])[C:5]1[C:4](=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH2:1]

Participants

4

Reactant 1

HCID 21543532HCID 21543532, compound

Product 1

HCID 21442848HCID 21442848, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5.75 G. (0.015 mol) of 2-(4-m-chlorophenyl-piperazino)-ethyl 2-nitrobenzoate in 100 ml. of methanol is hydrogenated at ambient temperature and at atmospheric pressure, in the presence of 1 g. of 10% palladium on charcoal. The theoretical amount of hydrogen (1 1.) is absorbed in 40 minutes. The catalyst is filtered off, the methanol is evaporated from the filtrate, and the residue is recrystallised from isopropyl alcohol to give 4 g. (yield = 74.1%) of 2-(4-m-chlorophenylpiperazino)-ethyl anthranilate, which melts at 77° and which was shown to be identical, using a mixed melting point, to the product of Examples 14 and 16.

Workup

  1. customis hydrogenated at ambient temperature and at atmospheric pressure, in the presence of 1 g
  2. customThe theoretical amount of hydrogen (1 1.) is absorbed in 40 minutes
  3. filtrationThe catalyst is filtered off
  4. customthe methanol is evaporated from the filtrate
  5. customthe residue is recrystallised from isopropyl alcohol
  6. customto give 4 g

Sources & evidence

ORD record
ord-3505d109c0f24d539488d2401a40cc1f
Source dataset
uspto-grants-1976_04
Patent number
US03953449

Reaction notes

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