4-Chlorobenzylpiperazine → HCID 13408413, compound

HRID 444218Notes

Reaction equation

HRID 444218 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH2:15]([C:18]1[C:19]([O:37][CH2:38][CH:39]2[O:41][CH2:40]2)=[CH:20][CH:21]=[C:22]2[C:27]=1[O:26][C:25](=[O:28])[CH:24]=[C:23]2[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:16]=[CH2:17]>C(O)C>[CH2:15]([C:18]1[C:19]([O:37][CH2:38][CH:39]([OH:41])[CH2:40][N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:8][CH2:9]2)=[CH:20][CH:21]=[C:22]2[C:27]=1[O:26][C:25](=[O:28])[CH:24]=[C:23]2[O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH:16]=[CH2:17]

Participants

4

Reactant 2

HCID 1348264-ChlorobenzylpiperazineHCID 13408410HCID 13408410, compound

Product 1

HCID 13408413HCID 13408413, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heating a mixture of 1-(4-chlorobenzyl)piperazine (6.2 g; 0.03 mole) and 8-allyl-4-benzyloxy-7-(2,3-epoxypropyloxy) coumarin (9.47 g; 0.026 mole) in ethanol (50 ml) to reflux for 2 hr and work-up as in Example 2(b) gave 7.85 g (52%) of the title compound of m.p. 155°-157° C., νmax (mull) 3320, 1675, 1615, 1605, 1565 cm-1 ; (Found; C, 69.04; H, 6.20; N, 4.67; Cl, 6.12; C33H35O5N2Cl requires; C, 68.92; H, 6.13; N, 4.87; Cl, 6.17%).

Workup

  1. temperatureHeating
  2. temperatureto reflux for 2 hr

Sources & evidence

ORD record
ord-c4c20840299f43b2a90d21f2d0446ba4
Source dataset
uspto-grants-1981_04
Patent number
US04263299

Reaction notes

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