Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate → tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

HRID 586486

반응식

HRID 586486 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 11243758Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate수율 83.4%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

4-(6-Nitro-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (83 g, 0.269 mol) in methanol (1.3 L) plus Raney Nickel (15 g, 50% slurry in water) were placed in a Parr shaker and hydrogenated at 50 psi of hydrogen for 5 h. The reaction mixture was filtered through a pad of celite and concentrated to a brown solid. This material was triturated with diethyl ether (120 mL) for 4 h. Heptane was added and the mixture was cooled to 0° C. for 45 min. The solid was collected by filtration and dried to afford the product 4-(6-amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester as a tan solid (62.46 g, 83%). mp 130-132° C. MS (ESI); M++1: Calc'd, 279.2. Found 279. Anal. Calc'd for C14H22N4O3: C, 60.41; H, 7.97; N, 20.13. Found; C, 60.45; H, 7.60; N, 19.87.

후처리

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated to a brown solid
  3. customThis material was triturated with diethyl ether (120 mL) for 4 h
  4. additionHeptane was added
  5. filtrationThe solid was collected by filtration
  6. customdried

출처 및 근거

ORD 기록
ord-4f300b84e6cc4c729ab895c6b3618eab
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936612B2

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