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4-Indol-1-yl-piperidine-1-carboxylic acid ethyl ester → 1-(1-methyl-piperidin-4-yl)-1H-indole

HRID 2258580
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반응식

HRID 2258580 반응식
C(O[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1
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참가 물질

4

반응물 2

HCID 140907494-Indol-1-yl-piperidine-1-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

생성물 1

HCID 140907431-(1-methyl-piperidin-4-yl)-1H-indole수율 64.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice cooled solution of 4-indol-1-yl-piperidine-1-carboxylic acid ethyl ester (50 g, 0.18 mol) in dry THF (400 mL) was added LAH in small portions (7 g, 0.18 mol). After 2 hours, the mixture was quenched by successive addition of water (7 mL) 15% of sodium hydroxide (7 mL) and water (21 mL). The reaction mixture was filtered. The filtrate was dried and evaporated. The residue crystallized on standing and was recrystallized from a small amount of di-i-propyl ether to give the title compound (25 g, 63% of theory). M.Pt.: 58° C.

후처리

  1. customthe mixture was quenched by successive addition of water (7 mL) 15% of sodium hydroxide (7 mL) and water (21 mL)
  2. filtrationThe reaction mixture was filtered
  3. customThe filtrate was dried
  4. customevaporated
  5. customThe residue crystallized
  6. customwas recrystallized from a small amount of di-i-propyl ether

출처 및 근거

ORD 기록
ord-c5bbfac97d4f4e5e90b9f1eda0b99d54
출처 데이터셋
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05661173

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