4-Chlorobenzylpiperazine → 1-[3-(4-Benzyloxycoumarin-7-yloxy)-2-hydroxypropyl]-4-(4-chlorobenzyl)piperazine

HRID 444215노트

반응식

HRID 444215 반응식
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:20][CH:21]3[O:23][CH2:22]3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:38]=[CH:37][C:29]([CH2:30][N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:28][CH:27]=1>C(O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:20][CH:21]([OH:23])[CH2:22][N:34]3[CH2:33][CH2:32][N:31]([CH2:30][C:29]4[CH:37]=[CH:38][C:26]([Cl:25])=[CH:27][CH:28]=4)[CH2:36][CH2:35]3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 1348264-ChlorobenzylpiperazineHCID 134084084-Benzyloxy-7-(2,3-epoxypropyloxy)coumarin

생성물 1

HCID 134084121-[3-(4-Benzyloxycoumarin-7-yloxy)-2-hydroxypropyl]-4-(4-chlorobenzyl)piperazine수율 62.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 4-benzyloxy-7-(2,3-epoxypropyloxy)coumarin (8.48 g; 0.026 mole), 1-(4-chlorobenzyl)piperazine (6.20 g; 0.0295 mole) and ethanol (50 ml) were refluxed together for 90 mins and allowed to cool. Evaporation of the solvent in vacuo gave an oily residue which crystallized on trituration with petrol ether. Recrystallization from methanol gave 8.67 g (62%) of title compound of m.p. 130°-133° C., νmax (mull) 1720, 1615 cm-1 ; δ (CDCl3) 2.55 (10H, m); 3.20 (1H, m); 3.48 (2H, s); 4.07 (3H broad s); 5.20 (2H, s); 5.68 (1H, s); 6.89 (2H, m); 7.30 (4H, s); 7.45 (5H, s); 7.77 (1H, d, J 10 Hz). (Found: C, 67.72; H, 6.00; N, 5.29; Cl, 7.21; C30H31N2ClO5 requires; C, 67.34; H, 5.84; N, 5.24; Cl, 6.63%).

후처리

  1. temperaturewere refluxed together for 90 mins
  2. temperatureto cool
  3. customEvaporation of the solvent in vacuo
  4. customgave an oily residue which
  5. customcrystallized on trituration with petrol ether
  6. customRecrystallization from methanol

출처 및 근거

ORD 기록
ord-1a0e7be5057f48f7a76558e8770c74e7
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04263299

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