Hydrochloric Acid → Methyl 3-(3-cyanophenyl)-5-[(piperidin-4-ylmethyl)aminomethyl]benzoate

HRID 1862573ノート

反応式

HRID 1862573 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH:19]=O)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[BH4-].[Na+].Cl>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 235274-(Aminomethyl)piperidineHCID 4311764Sodium borohydrideHCID 9795280Methyl 3-(3-cyanophenyl)-5-(formyl)benzoate

生成物 1

HCID 18620001Methyl 3-(3-cyanophenyl)-5-[(piperidin-4-ylmethyl)aminomethyl]benzoate収率 71%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

In 30 ml of toluene, were dissolved 3.00 g of the compound obtained in Example 11 and 1.50 g of 4-aminomethylpiperidine. The resulting solution was refluxed for 3 hours to remove the produced water. The solvent was evaporated from the reaction solution under reduced pressure, and 10 ml of tetrahydrofuran and 20 ml of methanol were added to the residue to provide a solution. To the resulting solution, was added 0.500 g of sodium borohydride under cooling with ice. The mixture was stirred at this temperature for 1 hour, then returned to room temperature and stirred for another hour. To the resulting solution was added a 1 M hydrochloric acid to quench the reaction. The resulting solution was washed with ethyl acetate. A 1 M aqueous solution of sodium hydroxide was added to the obtained aqueous layer until the pH attained 10. The resulting solution was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and subsequently dried over sodium sulfate, and the solvent was removed under reduced pressure to provide 2.9 g (71%) of the title compound as an oil.

後処理

  1. temperatureThe resulting solution was refluxed for 3 hours
  2. customto remove the produced water
  3. customThe solvent was evaporated from the reaction solution under reduced pressure, and 10 ml of tetrahydrofuran and 20 ml of methanol
  4. additionwere added to the residue
  5. customto provide a solution
  6. temperatureunder cooling with ice
  7. customreturned to room temperature
  8. stirringstirred for another hour
  9. customto quench
  10. customthe reaction
  11. washThe resulting solution was washed with ethyl acetate
  12. additionA 1 M aqueous solution of sodium hydroxide was added to the obtained aqueous layer until the pH
  13. extractionThe resulting solution was extracted with ethyl acetate
  14. washThe resulting organic layer was washed with saturated brine
  15. dry with materialsubsequently dried over sodium sulfate
  16. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-78b920ed63544df6b69a110c89bebac4
出典データセット
uspto-grants-2003_03
特許番号
US06538137B1

反応ノート

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