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

HRID 444215Notes

Reaction equation

HRID 444215 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-1a0e7be5057f48f7a76558e8770c74e7
Source dataset
uspto-grants-1981_04
Patent number
US04263299

Reaction notes

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