Mechlorethamine → 3-(4-Fluorophenyl)-5-methyl-1-(1-methylpiperazin-4-yl)-1H-indole

HRID 275364

반응식

HRID 275364 반응식
[NH2:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:3]1.[NH2-].[Na+].Cl[CH2:22][CH2:23][N:24]([CH3:28])[CH2:25][CH2:26]Cl>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=3)[N:2]([N:1]3[CH2:26][CH2:25][N:24]([CH3:28])[CH2:23][CH2:22]3)[CH:3]=2)=[CH:13][CH:14]=1

참가 물질

6

반응물 3

HCID 4033MechlorethamineHCID 24533Sodium amideHCID 100830041-Amino-3-(4-fluorophenyl)-5-methyl-1H-indole

생성물 1

HCID 102456373-(4-Fluorophenyl)-5-methyl-1-(1-methylpiperazin-4-yl)-1H-indole

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 7237O-Xylene용매

실험 절차

To a mixture of 1-amino-3-(4-fluorophenyl)-5-methyl-1H-indole 19a (1 g) and toluene (20 ml) was added a 50% suspension of sodium amide in xylene (1.0 ml). After reaction for 15 min at room temperature a solution of N,N-bis(2-chloroethyl)methylamine (0.8 g) in toluene was added slowly and the mixture was refluxed for 3 h. After cooling to room temperature, the solvents were evaporated in vacuo and water (100 ml) was added. The mixture was extracted with ethyl acetate (2×50 ml) and the combined organic phases were dried (Na2SO4). Evaporation of the solvents in vacuo afforded the title compound, which was purified by column chromatography on silica gel (eluted with ethyl acetate/ethanol 4:1 containing 4% triethylamine) and crystallized from heptane. Yield: 0.5 g, mp 105°-107° C.

후처리

  1. additionwas added slowly
  2. temperaturethe mixture was refluxed for 3 h
  3. customthe solvents were evaporated in vacuo and water (100 ml)
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  6. dry with materialthe combined organic phases were dried (Na2SO4)
  7. customEvaporation of the solvents in vacuo

출처 및 근거

ORD 기록
ord-033f78d445534a13a9f2f1d514996018
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393761

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