Iodide Ion → Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

HRID 507371

반응식

HRID 507371 반응식
I[C:2]1[CH:15]=[C:14]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Cu][C:17]#[N:18].[I-]>CN1CCCC1=O>[CH3:12][N:11]([CH2:10][CH2:9][C:8]1[C:14]2[C:5](=[CH:4][CH:3]=[C:2]([C:17]#[N:18])[CH:15]=2)[NH:6][CH:7]=1)[CH3:13]

참가 물질

5

반응물 3

HCID 30165Iodide IonHCID 136913602-(5-Iodo-1H-indol-3-yl)-N,N-dimethylethanamineHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 28511Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-수율 82.4%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
180 °C

실험 절차

A flask with mechanical stirrer is charged with 5-iodo-dimethyltryptamine (179 g of 75% purity, 0.427 mol), copper (I)cyanide (90 g, 1.0 mol), and N-methylpyrrolidone (1.5 l). The pink suspension is heated at 180° C. under a nitrogen atmosphere and vigorously stirred, until the iodide is completely consumed (7 h). After cooling to ambient temperature ammonia (2 l 25% solution in water) is added, and the resulting mixture is stirred over night. The mixture is then extracted with TBME (6*1.5 l), and the combined organic layers are washed with water (3*3 l), and brine (1*3 l), and dried (sodium sulfate). Removal of the solvent leaves 75 g (82%) of the product which is >95% pure by HPLC (other properties cf. Reference Example 3).

후처리

  1. customis completely consumed (7 h)
  2. temperatureAfter cooling to ambient temperature ammonia (2 l 25% solution in water)
  3. additionis added
  4. extractionThe mixture is then extracted with TBME (6*1.5 l)
  5. washthe combined organic layers are washed with water (3*3 l), and brine (1*3 l)
  6. dry with materialdried (sodium sulfate)
  7. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-47f4acba52e7425fa01c7da171f52bed
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786156B2

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