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

HRID 845417Notes

Reaction equation

HRID 845417 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fb47d4eeb0d4450c9e47fc0d2d2546e8
Source dataset
uspto-grants-1988_07
Patent number
US04758568

Reaction notes

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