Ammonia → 4-(Piperidin-3-yl)-1H-indole

HRID 1155683노트

반응식

HRID 1155683 반응식
[Li].N.Cl.[NH:4]1[C:12]2[C:7](=[C:8]([C:13]3(O)[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.O1CCCC1>C(O)C>[NH:15]1[CH2:16][CH2:17][CH2:18][CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:7]=2[CH:6]=[CH:5][NH:4]3)[CH2:14]1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 3028194LithiumHCID 12900686HCID 12900686, 화합물

생성물 1

HCID 30677184-(Piperidin-3-yl)-1H-indole수율 69.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

700 mg of lithium were added in small fractions over one hour at -40° C. to a mixture of 100 ml of ammonia, 1.2 g of 3-(1H-indol-4-yl)-3-piperidinol hydrochloride, 20 ml of tetrahydrofuran and 10 ml of anhydrous ethanol and the ammonia was evaporated at room temperature. The residue was taken up in 100 ml of water and the aqueous phase was extracted with chloroform containing 10% methanol. The organic phase was washed with water, dried and filtered. The filtrate was evaporated to dryness and the 950 mg of residue was chromatographed over silica gel. Elution with a 7-2-1-chloroform-methanol-triethylamine mixture yielded 665 mg of 4-(piperidin-3-yl)-1H-indole.

후처리

  1. customthe ammonia was evaporated at room temperature
  2. extractionthe aqueous phase was extracted with chloroform containing 10% methanol
  3. washThe organic phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe 950 mg of residue was chromatographed over silica gel
  8. washElution with a 7-2-1-chloroform-methanol-triethylamine mixture

출처 및 근거

ORD 기록
ord-878a87cde2ab4eaa863a2bca5ecc1717
출처 데이터셋
uspto-grants-1982_06
특허 번호
US04332808

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