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Dimethylcarbamoyl Chloride → 1-(6-Dimethylaminocarbonylaminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine

HRID 1884839
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인쇄 미리보기

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HRID 1884839 반응식
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][N:33]([CH3:37])[C:34](Cl)=[O:35]>C1COCC1>[CH3:32][N:33]([CH3:37])[C:34]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)=[O:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 235048071-(6-Aminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine

생성물 1

HCID 235047741-(6-Dimethylaminocarbonylaminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1-(6-Aminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine, 2a (3 g) was dissolved in THF (50 ml) and triethylamine (2 g) was added. At 5° C. dimethylcarbamoylchloride (1 g) in THF (15 ml) was added dropwise. After completed addition the mixture was refluxed for 1.5 hours. THF was evaporated. Water was added and extraction with dichloromethane (2×50 ml) and work-up as above of the combined organic phases yielded crude title product, which was purified by column chromatography on silica gel (eluted with 4% triethylamine in a 1:1 mixture of ethyl acetate and heptane). The pure title compound 6a crystallized from diethyl ether. Yield : 1,4 g, mp: 141-144° C. 1H NMR (CDCl3): δ 1.65-2.55 (m, 10H); 2.70 (dd, 1H); 2.70-2.95 (m, 2H); 2.95-3.05 (m, 1H); 3.05 (s, 6H); 3.15 (broad d, 1H); 3.35 (qui, 1H); 6.25 (s, 1H); 6.95-7.25 (m, 6H); 7.45 (s, 1H)

후처리

  1. additionaddition the mixture
  2. temperaturewas refluxed for 1.5 hours
  3. customTHF was evaporated
  4. additionWater was added
  5. extractionextraction with dichloromethane (2×50 ml)

출처 및 근거

ORD 기록
ord-768ab707da8d49b5a0021f9ba6a38d0b
출처 데이터셋
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06767907B2

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