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

HRID 416778

反応式

HRID 416778 の反応式
N1C=C[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(O)C)=[CH:24][CH:23]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(N1CCNCC1)(OC(C)(C)C)=O>CCOC(C)=O.CO.CS(C)=O.C(Cl)Cl>[N:22]1[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:24][CH:23]=1

参加物

9

反応物 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90919alpha-Methyl-4-pyridinemethanolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 60137623tert-Butyl 4-(1-(pyridin-2-yl)ethyl)piperazine-1-carboxylate2 回

生成物 1

HCID 46868084tert-Butyl 4-(1-(pyridin-4-yl)ethyl)piperazine-1-carboxylate

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒HCID 21584119Ethylacetate methanol溶媒

実験手順

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-4-yl)ethanol (J. Chem. Soc., Perkin Trans. 1, 2000, 4439-4444) (100 mg, 0.81 mmol), triethylamine (5.0 eq, 4.05 mmol, 0.56 mL), MsCl (2.0 eq, 1.62 mmol, 0.13 mL), CH2Cl2 (4 mL) at 0° C. for 30 minutes, then N—BOC piperazine (4.0 eq, 3.24 mmol, 605 mg), DMSO (3 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 (163 mg, 69% for two steps) as a colourless oil; 1H-NMR (500 MHz, CDCl3) 1.50 (s, 9H, C(CH3)3), 1.72 (s, br, 3H, CH3), 2.42-2.60 (m, 4H, piperazine N(CH2)2), 3.49 (s, br, 5H, CH & piperazine N(CH2)2), 7.32 (d, J=5.7 Hz, 2H, pyridine H-3 & H-5), 8.59 (d, J=5.7 Hz, 2H, pyridine H-2 & H-6);

後処理

  1. customThis was prepared
  2. customat 0° C.
  3. customfor 30 minutes
  4. customgave the product (163 mg, 69% for two steps) as a colourless oil

出典と根拠

ORDレコード
ord-b9b7d9100cc74dae9ea321106d3a7f6a
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

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