Sodium hydride → 1-[3-(4-Benzyloxycoumarin-7-yloxy)propyl]-4-(4-chlorobenzyl)piperazine

HRID 444212Notes

Reaction equation

HRID 444212 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Na].[Cl:24][C:25]1[CH:41]=[CH:40][C:28]([CH2:29][N:30]2[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38]Cl)[CH2:32][CH2:31]2)=[CH:27][CH:26]=1>>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:38][CH2:37][CH2:36][N:33]3[CH2:34][CH2:35][N:30]([CH2:29][C:28]4[CH:27]=[CH:26][C:25]([Cl:24])=[CH:41][CH:40]=4)[CH2:31][CH2:32]3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 5360545SodiumHCID 133997271-[(4-Chlorophenyl)methyl]-4-(3-chloropropyl)piperazineHCID 134084074-Benzyloxy-7-hydroxycoumarin

Product 1

HCID 134084141-[3-(4-Benzyloxycoumarin-7-yloxy)propyl]-4-(4-chlorobenzyl)piperazineYield 74.3%

Procedure

To a solution of 4-benzyloxy-7-hydroxycoumarin (9.4 g, 0.035 mole) in dry NN-dimethylformamide (35 ml) was added sodium hydride (0.84 g; 0.035 mole) and the mixture stirred for 1 hour at 100° to complete formation of the sodium salt. To this was added a solution of 1-(4-chlorobenzyl)-4-(3-chloropropyl)piperazine (9.3 g; 0.035 mole) in dry NN-dimethylformamide (40 ml) over 1 hour and the resulting mixture stirred for 4 hours at 100°. The precipitated sodium chloride was filtered from the cooled mixture and the filtrate evaporated in vacuo to a red oil which was extracted with dry ether. Concentration of the extracts afforded 13.5 g (74%) of white crystalline material of m.p. (EtOH) 115°-116°, νmax (mull) 1725, 1625, 1610 cm-1. δ (CDCl3) 2.01 (2H, m); 2.48 (10H, m); 3.46 (2H, s); 4.07 (2H, t, J 6 Hz); 5.17 (2H, s); 5.65 (1H, s); 6.80 (2H, s); 7.27 (4H, s); 7.43 (5H, s); 7.72 (1H, d, J 9.6 Hz). (Found; C, 69.23; H, 6.12; Cl, 7.00; N, 5.22; C30H31ClN2O4 requires; C, 69.42; H, 6.02; Cl, 6.83; N, 5.40%).

Workup

  1. stirringthe resulting mixture stirred for 4 hours at 100°
  2. filtrationThe precipitated sodium chloride was filtered from the cooled mixture
  3. customthe filtrate evaporated in vacuo to a red oil which
  4. extractionwas extracted with dry ether

Sources & evidence

ORD record
ord-7d195956b0704a38b1352dcd36a73935
Source dataset
uspto-grants-1981_04
Patent number
US04263299

Reaction notes

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