1-Phenylpiperazine → 1-[5-(3,4-Dimethylphenyl)-furan-2-ylmethyl]-4-phenylpiperazine

HRID 1112744노트

반응식

HRID 1112744 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH:14]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO.Cl.C([BH3-])#N.[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH2:14][N:25]3[CH2:26][CH2:27][N:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:23][CH2:24]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

참가 물질

6

반응물 4

HCID 70961-PhenylpiperazineHCID 9601395-(3,4-Dimethylphenyl)furan-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanol

생성물 1

HCID 227625161-[5-(3,4-Dimethylphenyl)-furan-2-ylmethyl]-4-phenylpiperazine

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

5-(3,4-Dimethylphenyl)-furan-2-carboxaldehyde (4.0g;0.02 mole), prepared by the method of C. S. Davis and G. S. Lougheed J.Het.Chem. 4,153, (1967), was added rapidly to a stirred solution of N-phenylpiperazine (3.2g; 0.02 mole) in methanol (30ml) adjusted to pH 7 (using MeOH/HCl). After 30 minutes a solution of sodium cyanoborohydride (0.48g; 0.0075 mole) in methanol (10ml) was added dropwise and the mixture stirred at room temperature for 2 hours. After removal of the methanol by evaporation, the resultant solid was purified by silica gel chromatography. The fractions containing the desired compound were combined, evaporated and the crystalline solid which formed was recrystallised from 60/80° C. petroleum ether to give the title compound, m.p. 110° C.

후처리

  1. customAfter removal of the methanol
  2. customby evaporation
  3. customthe resultant solid was purified by silica gel chromatography
  4. additionThe fractions containing the desired compound
  5. customevaporated
  6. customthe crystalline solid which formed
  7. customwas recrystallised from 60/80° C. petroleum ether

출처 및 근거

ORD 기록
ord-10bd93d474fe453dabfd23b6c88cdfec
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04123529

반응 노트

불러오는 중…