Triethylamine → tert-Butyl 4-(1-(pyridin-3-yl)ethyl)piperazine-1-carboxylate

HRID 416775

반응식

HRID 416775 반응식
N1C=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH3:8].[N:22]1C=CC=C(C(O)C)[CH:23]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(N1CCNCC1)(OC(C)(C)C)=O>CS(C)=O.CCOC(C)=O.CO.C(Cl)Cl>[N:22]1[CH:5]=[CH:4][CH:3]=[C:2]([CH:7]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]2)[CH3:8])[CH:23]=1

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 101192alpha-Methyl-3-pyridinemethanolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 60137623tert-Butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate2회

생성물 1

HCID 66622025tert-Butyl 4-(1-(pyridin-3-yl)ethyl)piperazine-1-carboxylate

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매HCID 21584119Ethylacetate methanol용매

실험 절차

This was prepared using the same procedure as for tert-butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate, but here using 1-(pyridin-3-yl)ethanol (J. Chem. Soc., Perkin Trans. 1, 2000, 4439-4444) (200 mg, 1.62 mmol), triethylamine (5.0 eq, 8.12 mmol, 1.13 mL), MsCl (2.0 eq, 3.25 mmol, 0.26 mL), CH2Cl2 (8 mL) at 0° C. for 30 minutes. A solution of ether-pentane (1:1, 20 mL) was added, the solid removed by filtration and the solvents removed in vacuo. The residue was then treated with N—BOC piperazine (4.0 eq, 6.50 mmol, 1.21 g) in DMSO (6 mL) at 60° C. for 18 h. Work up as described for tert-butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate, followed by column chromatography (EtOAc-MeOH, 95:5) gave the product (186 mg, 39% for two steps) as a colourless oil; 1H-NMR (500 MHz, CDCl3) 1.36 (d, J=6.8 Hz, 3H, CH3), 1.42 (s, 9H, C(CH3)3), 2.29-2.45 (m, 4H, piperazine N(CH2)2), 3.38 (t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.45 (q, J=6.8 Hz, 1H, CH), 7.23 (dd, br, J=7.9, 4.7 Hz, 1H, pyridine H-5), 7.64 (dt, J=7.8, 1.9 Hz, 1H, pyridine H-4), 8.47 (dd, J=4.8, 1.8 Hz, 1H, pyridine H-6), 8.52 (d, br, J=1.9 Hz, 1H, pyridine H-2);

후처리

  1. customThis was prepared
  2. customat 0° C.
  3. customfor 30 minutes
  4. customthe solid removed by filtration
  5. customthe solvents removed in vacuo
  6. customgave the product (186 mg, 39% for two steps) as a colourless oil

출처 및 근거

ORD 기록
ord-eb915e51ed0f4cb4b0239007b64ae9a0
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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