Triethylamine → 4-Amino-6,7-dimethoxy-2-[4-(isobutoxycarbonyl)-piperazin-1-yl]quinoline hydrochloride sesquihydrate

HRID 542210

반응식

HRID 542210 반응식
[CH2:1]([O:5][C:6]([Cl:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[C:12]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:11]=1.C(N(CC)CC)C.C(=O)([O-])[O-:38].[Na+].[Na+]>C(Cl)(Cl)Cl>[OH2:5].[ClH:8].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[C:12]([N:24]2[CH2:25][CH2:26][N:27]([C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:7])[CH2:28][CH2:29]2)[CH:11]=1.[OH2:38].[OH2:5].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[C:12]([N:24]2[CH2:25][CH2:26][N:27]([C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:7])[CH2:28][CH2:29]2)[CH:11]=1.[ClH:8]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 62365Isobutyl chloroformateHCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

생성물 1

HCID 1317150914-Amino-6,7-dimethoxy-2-[4-(isobutoxycarbonyl)-piperazin-1-yl]quinoline hydrochloride sesquihydrate

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

A solution of isobutylchloroformate (0.11 g) in chloroform (5 ml) was added dropwise to a stirred solution of 4-amino-6,7-dimethoxy-2-[piperazin-1-yl]quinoline (0.21 g) in chloroform (15 ml) with triethylamine (0.22 g) at 10°. The solution was then stirred at room temperature for 1 hour and sodium carbonate solution (10%, 10 ml) added. The organic phase was separated, the aqueous solution extracted with chloroform (2×15 ml) and the total combined extracts dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography on silica gel (Merck 9385, 25 g) eluting with methylene chloride-methanol (100:0→93:7), followed by treatment of the product with ethereal hydrogenchloride and recrystallisation from isopropanol to give 4-amino-6,7-dimethoxy-2-[4-(isobutoxycarbonyl)-piperazin-1-yl]quinoline hydrochloride sesquihydrate, m.p. 254°-256° (0.065 g).

후처리

  1. customThe organic phase was separated
  2. extractionthe aqueous solution extracted with chloroform (2×15 ml)
  3. dry with materialthe total combined extracts dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel (Merck 9385, 25 g)
  6. washeluting with methylene chloride-methanol (100:0→93:7)
  7. customfollowed by treatment of the product with ethereal hydrogenchloride and recrystallisation from isopropanol

출처 및 근거

ORD 기록
ord-c43c6bccb2c34bc69377397fd77818c3
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04656174

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