3-Furoic acid → 1-[(2-Furanyl)carbonyl]-4-(6-methoxy-indan-1-yl)piperazine

HRID 1956158Notes

Reaction equation

HRID 1956158 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1.[O:18]1C=C[C:20](C(O)=O)=[CH:19]1.[OH:26]N1C2C=CC=CC=2N=N1.C(N=C=N[CH:42]([CH3:44])[CH3:43])(C)C>ClCl.CN(C=O)C>[O:18]1[CH:19]=[CH:20][CH:44]=[C:42]1[C:43]([N:15]1[CH2:14][CH2:13][N:12]([CH:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=3)[CH2:7][CH2:8]2)[CH2:17][CH2:16]1)=[O:26]

Participants

7

Reactant 4

HCID 102683-Furoic acidHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 22038119(6-Methoxy-indan-1-yl)piperazine

Product 1

HCID 223753971-[(2-Furanyl)carbonyl]-4-(6-methoxy-indan-1-yl)piperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24526ChlorineSolvent

Procedure

A solution of (-)-(6-methoxy-indan-1-yl)piperazine (28 mg, 0.12 mmol), 3-furoic acid (58 mg, 0.52 mmol), and 1-hydroxybenzotriazole (17 mg, 0.126 mmole), and 1,3-diisopropylcarbodiimide (16 mg, 0.126 mmol) in CH2 Cl2 (2 ml) and DMF (2 ml), was shaken for for 5 min and allowed to stand for 18 hr. The reaction mixture was filtered through an SCX Bondesil® (Varian # 1221-3039, 1 g) column. The column was washed with methanol (20 ml) and 0.1N NH4OH in methanol (2 ml). The product was then eluted from the column using 1N NH4OH in methanol (5 ml). This last fraction was concentrated in vacuo to give the product (36.8 mg, 94%, ES-MS: 327 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through an SCX Bondesil® (Varian # 1221-3039, 1 g) column
  2. washThe column was washed with methanol (20 ml) and 0.1N NH4OH in methanol (2 ml)
  3. washThe product was then eluted from the column
  4. concentrationThis last fraction was concentrated in vacuo
  5. customto give the product (36.8 mg, 94%, ES-MS

Sources & evidence

ORD record
ord-c2943da7f39141e6b58dde35ea31a602
Source dataset
uspto-grants-1998_07
Patent number
US05780470

Reaction notes

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