4-(Chloromethyl)pyridinium chloride → 1,3-dihydro-1-(4-morpholinyl)-3,3-bis(4-pyridinyl methyl)-2H-indol-2-one

HRID 22232

反応式

HRID 22232 の反応式
[N:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2=[O:16])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.[N:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=1.O.C(Cl)(Cl)Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.[OH-].[Na+]>[N:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:24][C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)([CH2:24][C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[C:8]2=[O:16])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

参加物

7

反応物 3

HCID 745704-(Chloromethyl)pyridinium chlorideHCID 152843961,3-dihydro-1-(4-morpholinyl)-2H-indol-2-oneHCID 22418719Chloroform water

生成物 1

HCID 152843971,3-dihydro-1-(4-morpholinyl)-3,3-bis(4-pyridinyl methyl)-2H-indol-2-one収率 88%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 1140Toluene溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 1,3-dihydro-1-(4-morpholinyl)-2H-indol-2-one (0.5 g, 2.3 mmole), 4-picolyl chloride hydrochloride (0.83 g, 5.0 mmole), benzyltriethylammonium chloride (0.053 g, 0.23 mmole) in toluene (5 ml) and 50% sodium hydroxide solution (3.6 ml) were heated at 70° C. for three hours. The reaction was cooled to room temperature and poured into water/chloroform (30 ml each). The layers were separated and the aqueous layer extracted with additional chloroform (3×20 ml). The combined organic layers were washed with water (50 ml), brine (50 ml), dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. The residue was chromatographed on silica gel using methanol/chloroform (7%), and recrystallized from chloroform/hexane to afford 0.81 g (88%) of the desired product as a solid, m.p. 200°-203° C.; IR (KBr): 1711 cm-1 ; 1H NMR (CDCl3, TMS) :δ8.26 (dd, J=4.4, 1.5Hz, 2H), 7.37 (m, 1H), dd, J =7.7, 1.4Hz, 2H), 6.80 (dd, J=4.4, 1.5Hz, 4H), 6.61 (dd, J=7.7, 1.1 Hz, 1H), 3.77 (dd, J=5.5, 1.1Hz, 2H), 3.59 (m, 2H), 3.43 (dd, J=11.4 Hz, 1.5Hz, 2H), 3.37 (d, J=12.8Hz, 2H), 3.14 (d, J=12.8Hz,2H), 2.01 (br.d, J =10.2Hz, 2H); mass spec. m/e 401 (M+H, 100%); Anal. (C24H24N4O2): C,H,N.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with additional chloroform (3×20 ml)
  4. washThe combined organic layers were washed with water (50 ml), brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customThe residue was chromatographed on silica gel
  9. customrecrystallized from chloroform/hexane

出典と根拠

ORDレコード
ord-f3fb8eb843ff4e899aa4fef472859b2c
出典データセット
uspto-grants-1995_06
特許番号
US05428035

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