Triethylamine → 1-[beta-(2-Methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine

HRID 26174

反応式

HRID 26174 の反応式
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.C(N(CC)CC)C.ClC(OCC)=O.[CH2:29]([C:36]1([OH:42])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][C:13]([N:39]1[CH2:38][CH2:37][C:36]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([OH:42])[CH2:41][CH2:40]1)=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 973801H-Indole-3-propanoic acid, 2-methyl-HCID 981524-Benzyl-4-piperidinol

生成物 1

HCID 213246711-[beta-(2-Methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a stirred solution of 5.0 g of β-(2-methyl-3-indolyl)propionic acid and 2.5 g of triethylamine in 100 ml of chloroform was added dropwise 2.7 g of ethyl chloroformate at a temperature below 0° C. After the addition was complete, stirring was continued for additional 15 minutes and thereto was added 4.7 g of 4-benzyl-4-hydroxypiperidine in several portions. The reaction mixture was stirred for 4 hours at room temperature and allowed to stand overnight. The reaction product was washed thoroughly with water and concentrated to dryness. The residue was recrystallized from ethanol to give 1-[β-(2-methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine, melting at 117°-119° C.

後処理

  1. additionAfter the addition
  2. stirringThe reaction mixture was stirred for 4 hours at room temperature
  3. waitto stand overnight
  4. washThe reaction product was washed thoroughly with water
  5. concentrationconcentrated to dryness
  6. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-3024e340990f494fa08720f195cbe64d
出典データセット
uspto-grants-1979_04
特許番号
US04148796

関連ノート

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