1-(3-Bromophenyl)propan-2-one → 5-{4-[2-(3-Bromophenyl)propyl]-1-piperazinyl)-2-methylquinoline

HRID 734562ノート

反応式

HRID 734562 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=O)C)[CH:5]=[CH:6][CH:7]=1.[CH3:12][C:13]1[CH:22]=[CH:21][C:20]2C(=[CH:16][CH:17]=[CH:18][C:19]=2[N:23]2[CH2:28][CH2:27][N:26]([CH2:29]CC3C=C(C=CC=3)N)[CH2:25][CH2:24]2)N=1.[C:38]([BH3-])#[N:39].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:9])[CH2:29][N:26]2[CH2:27][CH2:28][N:23]([C:19]3[CH:18]=[CH:17][CH:16]=[C:38]4[C:20]=3[CH:21]=[CH:22][C:13]([CH3:12])=[N:39]4)[CH2:24][CH2:25]2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 27340931-(3-Bromophenyl)propan-2-oneHCID 5003444Sodium cyanoborohydrideHCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

生成物 1

HCID 574443285-{4-[2-(3-Bromophenyl)propyl]-1-piperazinyl)-2-methylquinoline収率 50%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

実験手順

A solution of zinc(II)chloride (0.5 M, THF, 0.5 eq., 234 uL) was added to a stirred solution of 1-(3-bromophenyl)-2-propanone (50 mg) and 2-methyl-5-(1-piperazinyl)quinoline (D3) (2.0 eq., 107 mg) in methanol (1 ml). The mixture was stirred 10 minutes then a solution of sodium cyanoborohydride (1M, THF, 1.0 eq., 234 uL) was added. The resulting white mixture was stirred at room temperature until hplc showed the complete disappearance of starting material. The mixture was concentrated under reduced pressure, diluted with aqueous sodium hydroxide solution (1M), and extracted with DCM. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The crude was purified by chromatography using a SPE cartridge (SiO2) with DCM-methanol (98:2) as eluent to afford the title compound (50 mg, 50% yield).

後処理

  1. stirringThe resulting white mixture was stirred at room temperature until hplc
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with aqueous sodium hydroxide solution (1M)
  4. extractionextracted with DCM
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude was purified by chromatography

出典と根拠

ORDレコード
ord-f008e7936e2e48619eb675a050f8c97a
出典データセット
uspto-grants-2009_09
特許番号
US07592346B2

反応ノート

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