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Dichloromethane → N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide

HRID 1352501
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HRID 1352501 반응식
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:21])[CH3:20])=[CH:10][CH:9]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl>CO.[B-](F)(F)(F)F.COC1C([P@](CC[P@](C2C=CC=CC=2)C2C(OC)=CC=CC=2)C2C=CC=CC=2)=CC=CC=1.C1CC=CCCC=C1.[Rh]>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:21])[CH3:20])[CH2:10][CH:9]1[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

5

반응물 2

HCID 6344DichloromethaneHCID 22935749N-(1-benzyl-2-methyl-1,2-dihydroquinolin-4-yl)-N-phenylacetamide

생성물 1

HCID 22935741N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide수율 79.6%

시약·촉매·용매 2

HCID 10930696(1Z,5Z)-cycloocta-1,5-diene;(R)-(2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane;rhodium;tetrafluoroborate촉매
HCID 887
Methanol
용매

실험 절차

A solution of N-(1-benzyl-2-methyl-1,2-dihydroquinolin-4-yl)-N-phenylacetamide (100 mg) and (R,R)-(−)-1,2-bis[(o-methoxyphenyl)(phenyl)phosphino]ethane(1,5-cyclooctadiene)rhodium (I) tetrafluoroborate (20 mg) in methanol (6 ml) was stirred under 20 bars of hydrogene overnight. Dichloromethane was added and the organic layer was washed by water and dried over sodium sulfate. The solvent was removed and the mixture was purified by chromatography on silica gel (dichloromethane/ethanol (99:1)) to afford N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide (80 mg).

후처리

  1. washthe organic layer was washed by water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed
  4. customthe mixture was purified by chromatography on silica gel (dichloromethane/ethanol (99:1))

출처 및 근거

ORD 기록
ord-7a65bf3093904768bfc6c7e4eaf63d2e
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07220760B2

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