Ammonia → HCID 20145272, compound

HRID 648664Notes

Reaction equation

HRID 648664 reaction equation
[NH2:1][C:2]([CH:4]([CH:17]([C:29]([NH2:31])=[O:30])[C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=O.N>N1C=CC=CC=1>[C:2]([CH:4]([CH:17]([C:29]([NH2:31])=[O:30])[C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][CH:28]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)#[N:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20145137HCID 20145137, compound

Product 1

HCID 20145272HCID 20145272, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
50 °C

Procedure

Two hundred thirty-four milligrams (1.22 m mol) of 4-toluene-sulfochloride were added in two batches to 520 mg (1.22 m mol) of ethyl 4-[(α-aminocarbonyl-2-piperidino-benzyl)-aminocarbonylmethyl]-benzoate in 0.22 ml of pyridine, and the mixture was heated to 50° C. After two hours and then one hour later, the same quantities of pyridine and 4-toluene-sulfochloride were again added, and the resulting mixture was heated for a further hour at 50° C. After the mixture was left to stand for two days at 20° C., 2N ammonia was added, and the mixture was extracted with chloroform. The chloroform solution was extracted twice with water. After drying and filtering, the solution was concentrated by evaporation in vacuo. The evaporation residue was purified by column chromatography on silica gel [chloroform/methanol (10:1)].

Workup

  1. temperaturethe resulting mixture was heated for a further hour at 50° C
  2. waitAfter the mixture was left
  3. waitto stand for two days at 20° C.
  4. extractionthe mixture was extracted with chloroform
  5. extractionThe chloroform solution was extracted twice with water
  6. customAfter drying
  7. filtrationfiltering
  8. concentrationthe solution was concentrated by evaporation in vacuo
  9. customThe evaporation residue was purified by column chromatography on silica gel [chloroform/methanol (10:1)]

Sources & evidence

ORD record
ord-b28a992594144f39b9da515ff9afa083
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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