Triethylamine → 1-Benzyl-4-[N-(o-nitrobenzyl)-amino]-piperidine dihydrochloride

HRID 67081

反応式

HRID 67081 の反応式
[ClH:1].Cl.[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:17]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)([O-:19])=[O:18].C(N(CC)CC)C.[BH4-].[Na+]>CO>[ClH:1].[ClH:1].[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N+:17]([O-:19])=[O:18])[CH2:12][CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 111012-NitrobenzaldehydeHCID 4311764Sodium borohydrideHCID 125944831-Benzylpiperidin-4-amine dihydrochloride

生成物 1

HCID 130510191-Benzyl-4-[N-(o-nitrobenzyl)-amino]-piperidine dihydrochloride収率 73.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In this reference example, 5.24 g of 1-benzyl-4-amino-piperidine dihydrochloride, 3.02 g of o-nitrobenzaldehyde, 2.02 g of triethylamine and 30 ml of methanol are mixed and stirred at room temperature for one hour. The resultant solution is cooled with ice and stirred. To the stirred solution, 1 g of sodium borohydride is added little by little over a period of one hour. Then, the mixture is brought back to room temperature and stirred at room temperature for 2 hours. The resultant solution is poured into 200 ml of ice water and extracted with ether. The organic layer is washed with water, dried and concentrated. The oily residue is dissolved in 20 ml of ethanol. The solution is mixed with 10 ml of a solution of 5.7 N hydrochloric acid in ethyl acetate. The white crystals deposited are separated by filtration, washed with 20 ml of ethyl acetate and dried to obtain 5.70 g of a crude product. The crude product is recrystallized from hot ethanol to obtain 2.90 g of the desired product.

後処理

  1. stirringstirred
  2. customis brought back to room temperature
  3. stirringstirred at room temperature for 2 hours
  4. extractionextracted with ether
  5. washThe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated
  8. dissolutionThe oily residue is dissolved in 20 ml of ethanol
  9. additionThe solution is mixed with 10 ml of a solution of 5.7 N hydrochloric acid in ethyl acetate
  10. customThe white crystals deposited are separated by filtration
  11. washwashed with 20 ml of ethyl acetate
  12. customdried
  13. customto obtain 5.70 g of a crude product
  14. customThe crude product is recrystallized from hot ethanol

出典と根拠

ORDレコード
ord-7acdca1f56324d87974902ede8121be3
出典データセット
uspto-grants-1982_08
特許番号
US04344948

関連ノート

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